


The Wedding Date

by killemwithfluff



Category: Supernatural
Genre: Eventual Smut, Fake/Pretend Relationship, Fights, Fluff, Movie Reference, Multi, Past Relationship(s), The Wedding Date, Weddings
Language: English
Status: Completed
Published: 2016-11-15
Updated: 2017-04-23
Packaged: 2018-08-31 03:35:24
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 17
Words: 39,104
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8562034
Author URL: https://archiveofourown.org/users/killemwithfluff/pseuds/killemwithfluff
Summary: With the wedding of one of his best friend's from his childhood approaching quickly, Castiel Novak is desperate to find a date to show his ex-fiance that his love life is just fine, thank you very much. However, when Castiel is forced to hire a male escort named Dean Winchester for his date, he finds new and old feelings he isn't quite sure what to do with.





	1. Chapter 1

“Come on, Charlie. You must help me.” Castiel Novak pleaded on the phone. He glared at the email on his screen, as if it was the email’s fault what it read, what it was reminding him of. The woman on the phone laughed. 

“No way. I love you, and I’d do anything for you, but I am NOT doing that.” Castiel heard the clicking of the keyboard at what had to be Charlie deciphering or coming up with some coding. That was all way over his head. He scrubbed his hand down his face, hoping that his coworkers couldn’t hear him from their own cubicles. The accounting firm that he worked at hadn’t sprung for sound proofing anything besides the partners’ offices, regardless of how confidential the information was that they worked with on a daily basis. 

“I’ll pay for everything! I’m sure my parents will even make you stay in another room so you don’t have to listen to me snore! Please, Charlie.” 

“Nope. Even if I wanted to, Dorothy and I have our anniversary trip to ComicCon next weekend.” Castiel groaned aloud. How could he forget the queens needed to return to their kingdom? 

“You’d get to meet my brothers!” Castiel threw out his last attempt. He always thought that his older brother Gabriel and his best friend Charlie Bradbury would become fast friends.

“That’s a low blow. You know I want to meet your family, but do you know how pissed Dorothy would be if I canceled our yearly voyage to the Motherland?” Charlie sighed, sympathetically. “You don’t have any other friends you want to spend a weekend with?”

“Not that I’d have as much fun with. Plus, some of them might expect something afterwards. I don’t want that.” 

“Why don’t you hire somebody? I just read this thing in one of Dorothy’s magazines that you can call these people and…”

“I’m not going to hire somebody to be my date.” Castiel whispered so that nobody would even hear that his friend had even suggested that. He ran his hand through his dark, already wild hair. 

“People do it all the time, Castiel. Plus, they’re professionals. They wouldn’t blow your cover like a certain redhead after a few drinks.” 

“You would never blow a cover, Charlie. You would see it as a quest to convince everybody that we’re madly in love. What’s the term you use? Lap-ring?” Charlie laughed, and then was suddenly silent and Castiel could practically see the eyeroll she threw at her cubicle mate, Harry, for shushing her. 

“LARPing, genius. I guess you’re probably right, but I’ll have my own lady love. Why is it so important that you bring somebody though?” 

“No reason.” Castiel became quiet. He didn’t want to say, but he figured Charlie would know.

“She’s going to be there isn’t she?” He was right. 

“Yeah, and I just don’t think I can face her alone.” Charlie sighed. 

“It’s been five years, Castiel. I think you could do it, but I can send you the article and get the info from Dorothy about which agency they interviewed, if you want.” Castiel paused and thought for a long moment. 

“I would greatly appreciate that. Thank you.” The rest of the day, Castiel’s thoughts were enveloped in his past, especially his romantic life that he had left back in his hometown. He’d thought that moving to Chicago would help him forget his heartbreak and maybe he would find the love of his life, but here he was, thinking about her again. Suddenly, the hurt came back and Castiel felt a pang in his blue eyes. He quickly wiped his eyes dry and threw himself back into his work until his watch beeped at him, informing him it was time to go home. 

YOU AND A GUEST ARE CORDIALLY INVITED TO ATTENDED THE WEDDING OF  
SARA BESS MYERS AND GARTH DONALD FITZGEARLD IV  
ON JULY 26TH OF THIS YEAR  
AT THE FIRST CHUCH OF GOD IN GRANTSBURG, WISCONSIN  
PLEASE REPLY NO LATER THAN JULY 11TH

Castiel stared at the invitation in his hands. Not only was there the wedding, but they were having a get together the night before and then brunch Sunday (which was what the email had reminded him of). Why had he said he had a plus one? 

He wasn’t that desperate. Was he? No, of course not. He had coworkers at the firm that could go with him. There was Zachariah’s (one of the partners) assistant, Anna. She was nice, and smart, and fairly pretty. The only issue would be if she had to work next weekend, which was entirely possible. Things didn’t slow down much in the city, and Zachariah could (and would) make her sit in on a meeting or two, even on the weekend. Maybe he could ask her tomorrow. Castiel fell into bed that night, hoping that he would have a dreamless sleep. 

“Good morning, Anna. How are you?” Castiel gave the woman sitting at the desk a smile the next morning on the way to his desk. She returned it, pushing her long red hair out of her eyes. 

“Good morning, Castiel. Well, thank you. How are you?” 

“Very well, thank you.” Anna gave a short nod and looked back at her computer. Castiel had contemplated all night, and decided to ask Anna at lunch to attend Bess’ wedding with him. However, now that he was standing in front of her, he decided to get it done with. “I have a question for you.”

“Oh.” Anna looked back to him. “Okay, what is it, Castiel?” Castiel took a deep breath before speaking. 

“I have a friend’s wedding next weekend, and I was curious if you would like to come with me.” Anna looked taken aback before gaining her composure. 

“Castiel, I’m very flattered, but I do have to work next weekend. Mr. Johnson has meetings all day Friday, and then Saturday he has a lunch meeting with important international clients.” Castiel kept his outwardly calm, but inside, he was disappointed. She had been his last hope. 

“Okay, I understand. Thank you for being honest.”

“I really am. Sorry that is.” 

“Oh no, really. I understand.” Anna seemed to breath in relief, and then gave Castiel a warm smile. 

“Good. Still on for lunch?” 

“Of course.”

That night, Castiel stared at the email from Charlie. There was no harm in just reading the article. Dorothy, a magazine editor, always had interesting articles featured. Castiel pulled his laptop towards him and opened the email. There was a link to the article and a phone number with another link to a website of what, Castiel assumed, was the agency that Dorothy had used for their inside look into the business. They were nice looking…models? Escorts? What should they be called exactly? Castiel scanned the article, seeing if there was an answer to his inquiry. The term ‘escorts’ was interchangeable with the term ‘paid companions’, at least in the article. 

Forty-five minutes later, Castiel was still staring at his laptop screen with his cell phone in his hand. He really didn’t need to do this. He could face everybody alone, couldn’t he? What was the worst that could happen? His elder brothers wouldn’t care. However, he also knew that they weren’t the reason that he was doing this. Castiel thought for another moment, before finally pushing the call button on his phone. 

“Good evening, and thank you for calling Crowley’s. This is Meg, how may I help you?” Castiel cleared his throat. 

“Hello, I was just…um…c…curious about…?”

“Aw, is this your first time?” The woman had exchanged her professional voice for a sultrier one. “Don’t worry, honey. This can be a lot of fun if you relax. Now, what kind of escort are you looking for?”

“Oh…um…I…I don’t know.” How had he not thought of this? How had he thought for nearly an hour and not thought of the kind of person he wanted? 

“Okay, well, let’s start with something easier. When would you need somebody?” 

“Friday, July 25th until Sunday, July 27th.” Castiel heard the clicking of a keyboard. 

“A bit of short notice.” Castiel figured he wasn’t supposed to hear that. “Oookay, and next question, would you prefer a male or female companion?” This question had made Castiel freeze. He hadn’t thought about that either. He had always assumed that there would only be female escorts, but he supposed that there were no pronouns used in the article that had suggested that this was a female only job. On the website, it was mostly filled with pictures of women, but now that he was looking at the website more thoroughly, he did notice that there was a section for male escorts that he hadn’t previously seen. He thought about the possibility of showing up with a male escort and thought that to see his family and friend’s faces would be rather comical. Still, he was choosing his battles this time around. 

“I would prefer a female.” Castiel replied. 

“Hm…okay.” There was more typing. “Well,” Meg huffed. “I…shoot. Okay. Give me just…” More clicking. “one…” clicking. “moment….oh. Well,” Meg hummed. “How opposed are you to a male companion?” Castiel thought for a moment. 

“Are you sure there’s…nobody else?” 

“I’m so sorry sir, but we only have one person available that weekend, and his name is Dean. Of course, the same rules would apply. Nothing would happen unless negotiated by the two of you and he would be as discreet as you would like him to be.” He didn’t need somebody that badly. He could simply tell Bess that his date had to cancel at the last minute. However, knowing Bess, she would ask for pictures and Castiel would have none to show. He could easily make a man work. Hell, he was going to take a lesbian to begin with. This didn’t have to be any different. He would just have to establish that nothing was going to happen. 

“And…how much would that cost?” Meg and Castiel began to discuss prices and what would and could be paid for by Castiel. Castiel had found a price that he was…happy wasn’t the right word, but could handle. He had been given Dean’s phone number so that they could find a time to meet before the weekend. 

He called the number the next morning and waited for somebody to answer on the other end. 

“This is Dean.” The voice threw him off. He wasn’t quite expecting the rough, deep tone. 

“Oh. Um…hello, Dean. This is Castiel. I was given this number by Meg.” 

“Well, hello Castiel. How are you?”

“I’m fine I suppose. I um…I am the person that is going to be…” What was he supposed to say? His date? 

“Oh right, the 25th through the 27th in Wisconsin?”

“Yes, and I was wondering if we could meet beforehand to discuss some things?” 

“That would be great idea. Does that Thursday work?”

“That should be fine.”

“Great, great, any time work best for you?” Castiel thought for a moment before he thought of the best time for him. 

“I think around seven-thirty would be ideal.” 

“Seeeeven-thiiiirty.” It sounded like Dean was writing this down. “Great. Any place specifically that you would like to meet?” Castiel quickly tried to think of bars around Chicago that none of his co-workers went (he would say friends, but to be honest, the only true friends he had were Charlie and Dorothy and they already knew that he was probably going to go through with the plan since they sent him the information). He thought about a place far enough away from the office and dirty enough that nobody would go to. 

“There’s a little dive bar on the corner of fifth and…”

“Dagwood’s?”

“Yes, there.”

“Alright. We can meet there at seven-thirty on Thursday. Can’t wait to meet you, Castiel.” Castiel didn’t know this Dean’s voice well enough, but he thought he heard a smile in there. Although, that could’ve just been the customer service (is that technically what you would call this business?) in him. 

“Goodbye, Dean.”

Castiel hung up the phone and tried to wrap his head around what he had just agreed to.


	2. Chapter 2

Castiel took a sip of his whiskey at the bar. It was the night before he was supposed to be leaving for Wisconsin and he was supposed be meeting this “Dean” person there. He had seen Dean’s picture on the website. It listed his height as 6’2, so slightly taller than Castiel. He had gorgeous green eyes that even Castiel was drawn to, and his short, dirty blond hair looked neat. He was a good-looking man. Castiel had to admit that.

They were supposed to be meeting to set up a story of how they met, how long they had been dating, things like that. He was over thirty minutes late. Castiel felt his phone vibrate in his jacket pocket. He quickly pulled it out to see that he had a text message. 

Sorry. Won’t be able to make it tonight. Will be at your house at nine tomorrow morning to drive to Wisconsin. -Dean

Castiel continued to look at his screen in shock. Dean was supposed to providing a service to Castiel. Castiel had paid for him to make this whole thing believable and now Dean wasn’t here? What kind of service is that? Castiel should file a complaint to this Crowley that runs the establishment. However, he supposed that would have to wait. 

Okay. -Castiel

Castiel wasn’t sure what else he could say. All he knew was that he was that he had to get through this weekend. He paid his tab and quickly left the bar.  
Castiel got very little sleep that night. He had debated aborting the whole idea multiple times that evening. Was impressing her so important that he was actually going to go through with this whole deception? Castiel heaved a heavy sigh thinking about why he actually was that desperate and why he couldn’t call the whole thing off. 

It wasn’t just going alone that he was worried about. Normally, returning home alone wouldn’t bother him, but Hannah was going to be there. Hannah was Castiel’s ex-fiancé. They had dated nearly all through high school and then after their senior year of college, Castiel proposed. Almost one year afterwards, things had become strained. Instead of talking about their problems and possibly making their relationship work, Hannah had simply left. She left a note saying that she couldn’t handle it anymore and wanted to leave, so she did. All her things were out of their apartment when Castiel came home from work one day. He found her at her mother’s house, but Hannah had no interest in fixing their problems, so Castiel left. Not just the apartment, but the city. He took his half of the money they had saved for their wedding and moved from Grantsburg, Wisconsin to Chicago, a big city that he could be anonymous. He found a job, an apartment, and started to move on with his life. He had stayed in touch with some friends from home, including Bess, whom he had known since he was five years old. He was so happy that she had found somebody. The only problem was that in a small town, everybody was friends with everybody, so Hannah and Bess had been friends too. 

Seven AM came far too soon. Castiel had fallen asleep around two, but five hours was not nearly enough time to be calm yet alert for what he was about to do. He pulled himself out of bed and looked outside. The sun was already completely up and shining through the window. Castiel proceeded to take a shower, dress in a pair of jeans and a white button up (the drinks that evening were casual and they began just after they were scheduled to arrive in Wisconsin), and made sure that his suit was still in the bag, even though he hadn’t taken it out since he’d gotten it back from the dry cleaners. He also counted out the seven thousand dollars that he had taken out of his savings account to pay for his date for the weekend. 

Castiel had just finished packing when he heard a knock at his front door. He checked his watch. 8:45 it read. Well, at least he came at all this time, early even. Castiel walked down his stairs and opened the door and was greeted by a man a couple inches taller than himself, wearing jeans, a black t-shirt, and aviator sunglasses. He had two cups of coffee from Starbucks in his hands. 

“Good morning, I’m Dean. I’d shake your hand, but,” Dean shrugged as he held up one of the cups. Castiel took it and then offered his now free hand to Dean’s. Dean took it with a smile.

“Thank you. I’m Castiel.” 

“Yeah, I figured that much.” Castiel didn’t like his attitude already. 

“Well, come inside.” Castiel took a step to the side, allowing Dean in. Once Dean was inside, Castiel shut the door and lead him to the kitchen. 

“I didn’t know what you’d want, so I just went with black coffee. Sorry about last night by the way, I…” Dean looked around the kitchen, appearing fascinated by it. 

“Black coffee is just fine, thank you.” Castiel took a sip, cutting off Dean. He really didn’t care why he was didn’t show last night, he was still a little irritated about it to be honest. 

“So,” Dean looked at Castiel and Castiel realized that he had taken off his sunglasses. His eyes were very green. Castiel had figured that the photos of the escorts had been altered, but when it came to Dean, that appeared to not be the case. “We’re going to Wisconsin you said?” Dean brought his own Starbucks cup to his lips, not moving his eyes.

“Y…yes. Grantsburg, Wisconsin. It’s my hometown.” Dean hummed, showing he was listening. “I…my family doesn’t think I’m gay or anything like that.” 

“We can work with that. Have you ever thought about being ya know…with another guy?” Dean still hadn’t looked away from Castiel, and Castiel’s face suddenly felt very warm. 

“Well…I…I haven’t…I mean, I had dated the same girl for most of high school and college.” Dean quirked a perfectly shaped eyebrow. 

“That wasn’t the question I asked. However, assuming by your stuttering and red face, I am going to go ahead and guess that yes, you have thought about it. You may not have acted on it, but you certainly have,” Dean paused and moved his eyes up and down Castiel’s body. Castiel felt like he was being objectified. “Thought about it. Now this girl that you mentioned, is she going to be there?” Castiel nodded. “And are we trying to win her back?” Castiel nearly choked on his coffee. He stared at Dean for a few seconds. Dean held up his hands. “Sorry, didn’t mean to cross a line.”

“No it’s not that, it’s just that I really haven’t thought about getting her back.” 

“We can figure it out on the way. We should probably get going, though. Drinks are at six, and it’s about a seven-hour car ride.” 

“I am aware of that. Would you like to put your items in my car or…?”

“Oh, well I was thinking we could take my car. It’s the least I could do after bailing last night.” Dean didn’t try to give an excuse this time. As much as Castiel appreciated the gesture, he didn’t want to know the kinds of things that had happened in that car. 

“Thank you, but I think it would be better if I drive.” Dean scoffed. 

“Look, man, I’m sure there’s some sentimental value to the car, but I have some standards about them and I am not showing up in a crappy, ’78 Continental.” Now Castiel was downright offended. 

“It’s not crappy. For your information that was my father’s favorite car. Besides, that isn’t what we would be taking. We would be taking my Prius.” Dean laughed this time. 

“Oh that’s even worse! No, we’re taking my car, end of discussion.” 

“Are you really in any position to be giving orders?” Castiel cocked an eyebrow of his own. He didn’t much like taking orders. Dean started walking closer.

“I’m in a great position to be giving orders. You see, you haven’t paid yet.” Dean and Castiel were practically touching when Dean bent down to whisper into Castiel’s ear. "So, I still hold a little bit of power, but after that, I’m completely at your mercy.” Dean had almost purred the last two words. And no, Castiel didn’t find it arousing at all. There was nothing about Dean’s warm breath in his ear or his body heat radiating from the closeness that made Castiel suddenly weak in the knees. Before Castiel could come to terms with what he was experiencing, Dean stepped away with a smirk. 

“I still do not understand why you want to drive.” Dean shrugged. 

“It makes me feel safe and I just really owe you for last night.” Castiel did think it was nice that Dean had offered to drive. 

“Okay. I suppose that’s fine.” Dean smiled. 

“Then let me show you my baby.” Baby…? Had Castiel heard him right? Who brings a baby along on something like this? Dean turned around and headed back out the front door. Castiel followed quickly, slightly nervous that he would have to explain not only that he was gay to his family, but his boyfriend had a child.  
In Castiel’s driveway was a car that looked like it was from the sixties, maybe seventies. Castiel had no idea. It was black and had sleek lines. It did look good, but Castiel didn’t see a child in the backseat, or even a car seat . Dean held out his arms and then turned back towards Castiel. 

“This is Baby. I’ve had her since I was seventeen. Built her from the ground up twice.” Dean was beaming. Meanwhile, Castiel breathed a sigh of relief. It was just his car. 

“Great. So we should get our things packed up and leave shortly.” Dean looked a little hurt that Castiel hadn’t been impressed with the rebuilding of the car, but he really didn’t care. Cars weren’t in Castiel’s wheelhouse. Castiel turned around and began to walk inside. Dean followed him. Castiel was about to grab his luggage when he remembered the stack of money on his dining room table. He continued into the dining room and came back to the kitchen with his envelope. 

“Seven thousand. Count it.” Dean started to tuck the money into his back pocket.

“I trust you.” 

“Count it. Please.” Dean shrugged and began counting. 

“…sixty-nine, seventy.” Dean held up the money. “All here. Thanks. Now, I know you said that you weren’t gay or anything, but if things were to get intimate, we’ll talk about money again.”

“Oh I am quite sure that we won’t need to have that conversation.” Castiel didn’t even attempt to keep the disgust out of his voice. 

“That’s what most people say, but we’ll see I suppose.” Dean ran his eyes up and down Castiel again. “Welp, we should probably get packed up and head out.” Castiel tried to push down the blush he could feel at the back of his neck. He really didn’t understand why the feelings were hitting him. Maybe he just wasn’t used to being in a relationship (real or pretend), so he was getting used to somebody looking at him like that again. The way Dean was looking at him though, he couldn’t even remember Hannah looking at him like that. Ever. Or perhaps he had been turned bitter to even the happy memories with her. Yes, that had to be it. Castiel tried to shake the feelings that made him think this was any more than a business transaction. 

Castiel gave a nod before going into the living room to grab his luggage. He took a deep breath and tried to focus while he was alone. He had just been thrown off guard by Dean and his attitude. That was all. He could do this. He had time to sort himself out. 

“Castiel?” Dean appeared near the doorway. “Are you okay?” Castiel picked up his bags. 

“Fine, thank you. Let’s get going.” Castiel looked at Dean. Dean nodded once and lead the way out the door.

**Notes for the Chapter:**

> Thank you guys so much for reading! Extra special thanks to SELIchan, Wt, allirose, and eshtiel (eshcaine) for your reviews for last chapter! Hope you enjoyed this one, too!


	3. Chapter 3

Once they had packed the (according to Dean anyway) Impala, Dean and Castiel made a stop at a gas station (which Castiel absolutely insisted on paying), and they finally were on their way to Wisconsin. 

“So,” Dean began once they hit the interstate. “Tell me who all I’m going to be meeting.”

“My parents, of course since we’ll be staying in their home. Two of my brothers. Gabriel and Michael. Raphael and Lucifer won’t be there. Actually, Gabriel will be staying in the house with us. Michael is the only one that stayed in town. Gabriel went to California. Lucifer went south somewhere. We haven’t talked to him in years. He had a bad fight with my dad when I was younger. Raphael moved to New York City to go to NYU for business and just stayed there. Then there’s Bess, who’s the bride. I’ve known her since I was five years old.” Castiel began rambling about who else Dean would be meeting but never went into any specifics, just names. 

“Okay, so let’s back track a little bit. Your parents. What are their names?” 

“Chuck and Becky.” 

“Got it. And your brothers are in what order?” 

“Michael, Lucifer, Raphael and then Gabriel.” 

“And finally you.”

“Yes.”  
“I figured you were the baby of the family.” Castiel looked over at Dean, confused. 

“Why?”  
“I just know what most babies of the family are like. You’re like them.” 

“What is that supposed to mean?” Dean shrugged. 

“It means what it means.” Castiel stared at the window for a long time. “So, are there more people I’m going to meet or…?”

“Oh sorry, just throwing a tantrum like a baby would.” Dean started laughing. This was the furthest thing from funny. 

“Sorry, it just…that is something…you know what? Never mind. Any other family secrets I need to know?”

“Secrets? There are no secrets.” Castiel snapped back. Dean simply didn’t say anything. Who the hell did this guy think he was? Calling Castiel a baby. Yes, he was the last child born to his parents, but he was no baby. He was on his way to be being partner at the firm, he paid for his OWN apartment in Chicago (no easy feat), he had a college degree. Dean had no idea who Castiel was. Who was he to be telling Castiel what he was and wasn’t?

The the car ride then filled with silence. Dean had attempted to get more information out of Castiel and Castiel answered his questions as simply as he could before going silent again. 

Dean had stopped trying to get information from Castiel near the Wisconsin border. Castiel cursed the fact that his family lived in northern Wisconsin for the umpteenth time in his life. Grantsburg sits practically on the border between Wisconsin and Minnesota. He hated the winters there. They took too long and were far too cold. Moving to Chicago, Castiel had gotten used to winters with less snow, so he was very happy when Bess had decided to get married in the summer. 

They stopped for gas nearly three hours into their journey, but once back inside the car, Dean began talking again. He started to pull out of the parking lot and back onto the interstate. 

“So what’s our story? How did we meet? How long have we been dating?” Oh. 

“Um…I…I don’t know. I hadn’t thought about that.” Dean chuckled. 

“You really haven’t done this before, have you?”

“I don’t plan on making this a habit.” Castiel retorted. Dean rolled his eyes.

“Alright,” Dean pulled the car over to the side of the road. Castiel widened his eyes and looked over to Dean. What was he doing? They needed to get going. Dean looked over at Castiel. “Look man, you’re going to have to drop this attitude by the time we get to your parents’ place otherwise this whole thing isn’t going to work.”

“What attitude?”

“This ‘holier than thou’ bullshit. Yes, I provide companionship for money. And yes, sometimes it does get physical, but that doesn’t make me any less of a person. I’m trying to do my job, but you’re going to have to help me a hell of a lot more than you are right now.” Castiel digested this. Thinking it wasn’t Dean’s job that annoyed him. It was Dean. However, he had a point. They only had a couple more hours (less with the way Dean was driving) left to complete their backstory. Castiel gave a sigh. 

“Fine, I understand and I apologize.” 

“Now was that so hard?” Dean’s smirk was back. Castiel was starting to wonder if Dean started to itch if he went so long without it reaching his lips. Dean put the car back in drive and went back into the lane and began speeding again. 

“Coffee shop.” He said suddenly. Dean’s profile looked surprised. 

“Coffee shop?”

“Yes, we met at a coffee shop. I spilled coffee on you and we started talking.”

“Really? You want to be the one that spills on me? Usually when I use that excuse I’m the one that messes up and you’re the one that’s nice enough to give me a chance.”

“Trust me. My family is going to eat it up.”

“So, you’re clumsy?” Castiel felt a minor blush come to his face. 

“Slightly. Plus, if somebody spilled coffee on me I would probably be too upset to start talking to them let alone ask them on a date.”

“Okay, good to know you’re kind of an asshole.” Castiel opened his mouth to reply, but Dean cut him off. “And how long have we been dating?”

“Bess’ invitations came out about six weeks ago and I said plus one then. So I suppose about three months?” The two continued to conspire, coming up with a nearly air tight fake relationship. Yes, it was surprising for Dean to ask Castiel out after that. No, they hadn’t said ‘I love you’ yet (“Trust me, they’ll ask” Castiel told Dean). No, they didn’t live together. Yes, Dean was Castiel’s first boyfriend. Castiel knew that people were going to ask more questions, but the other ones were probably going to be directed to Dean about who he was and why he was with Castiel. 

“What do you think their reaction going to be? You sort of coming out?” Castiel shrugged. 

“Honestly, I don’t know if they’ll actually say anything to me. Despite my brothers and I being named after angels, my family is very open. Well, my immediate family, anyway.” 

“Good to hear.” 

Castiel came up with a few more instances (“If Gabriel asks you to go for drinks say no” “If Michael asks you anything personal just ignore him”) before they needed to stop again, just short of Grantsburg. 

“Okay, last time, is there anything else that I need to know?” Castiel hesitated before taking a deep breath. 

“Yes. You know how most families you love them because they’re your family even though they’re crazy?” Dean nodded. 

“Mine’s not like that. Most of the time, if they see a weakness they’ll go after it. Especially Michael. Gabriel will prank you like it’s his job, either in word play or actually physically as though we’re in middle school, for just desserts as he calls them. Under no circumstances are you to be alone with any of them. They will try to get information out of you. Things that we haven’t talked about.”

“You know, I am pretty good at lying.” Castiel set his jaw.

“I understand that, but this is different. They’ll purposefully bring up an embarrassing story about me when I was younger and then change something to see if you know the story or not. I know how they operate. They use it as an act. As if it’s all to protect me, and maybe, in Gabriel’s case, it’s true. I think the other three just enjoy seeing people suffer.” Dean let out a low whistle. 

“Damn, that’s uh…that’s harsh.” Castiel let out a bitter blast of laughter. 

“You don’t know harsh until you hear my mother say something about me and Hannah. You’ll get compared to her, by the way. Even though this is a totally different situation, she won’t care. She loved Hannah so much and she was so excited to have a daughter-in-law.” Castiel sighed. He was grateful that Dean didn’t ask any more questions. They rode in silence as Castiel thought of what his mother would say about Dean. Comparing Dean to ‘perfect Hannah’. How Castiel would probably ‘chase this one away’ too. Weren’t mothers supposed to be on your side after a break up? Particularly one that you didn’t see coming? One that you didn’t instigate besides the fact that the relationship was having some problems? Castiel bit the inside of his cheek. He really loved his mother and he knew that she loved him, but the way she showed that she was upset about Castiel and Hannah’s break up didn’t make him feel better. His father had given him a hug and let him know that no matter what he needed, Chuck would get it for him. Michael hadn’t said anything when Castiel told him. He simply glossed over the subject. Gabriel had talked on the phone with Castiel for nearly three hours afterwards. Most of it had been Castiel crying and Gabriel telling him that she wasn’t worth it. Gabriel had told Castiel that he never liked Hannah, which was a lie, but Castiel appreciated the sentiment. 

“Home sweet home.” Dean beamed at the sign that read ‘The People of Grantsburg Welcome You!’. 

Castiel’s heart started pumping faster as he and Dean slowly made their way through the town, bringing them closer to Castiel’s parents’ home. He suddenly felt a warm, solid presence on his knee. He looked down and noticed that it was Dean’s hand. 

“Stop bouncing. It’s driving me crazy.” When had he started bouncing his knee? Castiel gently pushed Dean’s hand off of him. 

“I will try. I apologize.” Dean pulled his hand back over and put it back on the steering wheel. 

“You really need to lock it up, man. What’s the worst that could happen?” Castiel stared at Dean in disbelief. 

“The worst that could happen is that my family finds out about this and I become more of an outcast in my hometown than I already am.” Perhaps that was a bit dramatic. Castiel wasn’t really an outcast. He was more…pitied. He hadn’t been home in the five years since he left, but his mother had told him people were asking about him. And the time before he left, all he saw in people’s eyes was pity. He didn’t need that again. 

“There’s much worse stuff than faking a relationship. I mean, your family will still love you. They might see you as a little bit desperate, but they won’t kick you out of the family."

Castiel was sure that Dean was joking, but it still didn’t make him feel better. Castiel kept his lip in a hard line until he noticed where they were. 

“Left up here.” Dean turned left and drove down the quiet street until they came upon 4627. They pulled into the massive driveway, big enough for three cars across, and Dean parked the car. Castiel looked into the mostly dark house. There were lights on in the living room. That meant his parents were home. He knew that they would be, but suddenly being this close made him even more nervous. What was he going to do? Why had he done this? Dean gently touched Castiel’s hand. Castiel jumped. 

“Hey,” Dean’s voice was gentle and Castiel looked over, into Dean’s eyes. How were they so green? There should be a color for the shade of his eyes. Wait, why was the color of his eyes so important? Because Charlie would ask, of course, Castiel justified it to himself. “Seriously, everything is going to be okay. You have to trust me and help me do my job.” Castiel nodded. Dean smiled a charming smile before climbing out of the car. Castiel knew that he was right. The two of them were going to have to trust each other on some level. Castiel took a deep breath before joining him.

**Notes for the Chapter:**

> Thank you guys so much for your kudos, reviews, and bookmarks. They really mean a lot to me. Hope you enjoyed this chapter, and I'll see you all next week!


	4. Chapter 4

Castiel and Dean were grabbing their bags out of the car when Castiel heard the front door open. He held his breath until he heard his mother’s voice. 

“Castiel? Sweetheart, is that you?” Dean gave Castiel’s arm a gentle squeeze and a nod, indicating that he was okay with Castiel leaving him at the trunk. Castiel stepped away from the car to see his parents, Chuck and Becky Novak. Chuck’s hair was starting to show more gray than brown and Becky’s light brown hair was showing signs of aging as well. He smiled at them as Becky opened her arms. “Ooooh. Honey, it’s so good to see you!” Becky practically squealed in his ear. 

“Hi, Mom.” Becky released her son and then Chuck brought him for a hug next. 

“Great to see you, son.” Chuck nearly whispered in his son’s ear. Once the two of them broke apart, Chuck began to look around. “So, where’s the plus one of yours?” Castiel felt himself break out into a cold sweat. 

“They…um…about that…it…” 

“Babe,” Dean appeared from behind the car. “Are you going to help me with the bags?” Castiel turned, his eyes growing as wide as saucers. Dean pulled out his charming smile again. “Oh, hello, you must be Mr. and Mrs. Novak.” Dean placed the bags down and reached his hand out to Chuck first, who didn’t seem to be fazed by his son bringing a man home. However, Becky, whose eyes looked very much like her son’s (in size anyway, Castiel had the blue eyes of his father instead of the odd blue/green combination of his mother) appeared as though she’d seen a ghost. Chuck took a step forward to shake Dean’s hand. 

“Wow, good hand shake. Please, it’s Chuck and Becky. Apparently our son forgot his manners.” Castiel shook his head. 

“Sorry. Mom, Dad, this is my,” Castiel tried not to stumble over the word. He had practiced it in his head a million times on the ride up, but saying it now still proved difficult. “Boyfriend, Dean. Dean, these are my parents, Chuck and Becky.” Becky’s mouth had closed, but her eyes had not shrunk in size as Castiel’s had. She reached her hand out and blinked. 

“Hi, I um…wow. You’re very…different than we pictured. I figured…I mean…Castiel, may I speak with you a minute?” 

“Dean, why don’t I help with those bags?” Chuck gave a warm smile, and then his eyes moved to the car. “This yours?” Dean nodded. “What is she? A sixty…?” 

“Seven. And I would love a hand, thank you, Chuck.” Dean and Chuck walked back to the car as Castiel was practically dragged inside by his mother. 

“So, this um…is quite the surprise.” Becky folded her arms across her chest, waiting for an answer. 

“Yes, I…um…I’ve been...it’s a long story, but I’m happy. Dean makes me happy.”

“So, he is your boyfriend?” Castiel nodded. Hearing that word again made him even more anxious. Like if the word was said enough times then the illusion the two of them were trying to create would be shattered. “I…I feel like this is something that should have been told to us before you got here. You know, this isn’t something that you just spring on your parents. What will everybody think?” The last sentence seemed to be meant just for Becky. 

“That I’m happier now?” Castiel began to offer, but Becky already turned her back to Castiel to go back to the kitchen. 

“We’ll see Michael at Pastor Jim’s barn. Gabriel should be here shortly. I’m just finishing up something small, you two must be hungry.” Becky called over her shoulder as the front door opened and Dean and Chuck came into the house. Dean gave a small whistle. 

Castiel was trying to pretend it didn’t bother him that his mother just flat out told him that this was a bad idea to bring Dean here. What did she know? 

“This is a great house, sir.” Dean’s eyes scanned the high ceilings in the two story, six bedroom, four bathroom home. “What is it you do, again?” 

“I’m a writer and Becky is my publicist. She…”

“Doesn’t get paid enough to deal with his crap!” Becky called from the kitchen. Chuck gave a small laugh. 

“She’s right about that. I’m sure you two want to settle in before we leave.” Chuck nodded up the stairs before leading Dean and Castiel up them. Castiel knew where he would be staying, but wondered if Dean would be in Raphael’s room since he wouldn’t be coming home. “Here we are.” Chuck put Castiel’s bag down. “Dean, if Castiel starts to snore you’re more than welcome to use one of the other rooms in the house.” Castiel heard the words, and they hit him like a ton of bricks. 

“Wait, do you mean that Dean and I are…in the same room?” Chuck knit his eyebrows together. 

“Well, your mother and I talked it over and decided that you two probably sleep in a bed together in Chicago, so why would this be different?” 

“We don’t live together.” Castiel couldn’t stop himself from saying quickly. Chuck continued to stare at his son curiously. “I…I suppose you’re right, though.” Castiel shot a nervous look to Dean. Dean just gave him a gentle smile before looking over to Chuck. 

“Thank you, Chuck. Castiel and I appreciate all of this.” 

“Of course, of course.” Chuck waved his hand at Dean in a ‘think nothing of it’ gesture and then turned his attention towards his son. “Gabriel should be here shortly. You two get settled and come downstairs when you’re ready.” 

“Okay, thank you, Dad.” Chuck gave Castiel and Dean a smile before leaving the room. Castiel quickly shut the door before staring at the bed for a moment before Dean cleared his throat. 

“I can uh…sleep on the floor. You kinda look like you might spontaneously combust at even the thought of this.” Dean nodded to the bed. 

“I just…I’m sorry. They usually made my brothers and their girlfriends from college stay in different rooms. I just thought it would be the same.” 

“You need to calm down, man.” 

“You keep saying that, but is it really your place to tell me that?” Dean rolled his eyes, and then looked at Castiel. 

“Close your eyes.” Castiel squinted and tilted his head. 

“Excuse me?” 

“Close. Your. Eyes.” Castiel gave Dean one more look before doing as he was told. Castiel felt Dean get closer and then he felt Dean’s breath in his ear. “Relax. Your family is going to believe this. Hannah is going to believe this. She is going to see how happy you are, and she is going to regret ever leaving you. I’m just here to help you enhance your own great features.” Castiel inhaled deeply and was suddenly overcome by the smell of Dean. There was a musky, natural smell with a slight spicy cologne, and another smell that Castiel couldn’t quite place. It oddly made him feel better. Castiel opened his eyes and was met by Dean’s, close enough that if either of them just leaned forward, their lips would touch (and no, Castiel’s mouth wasn’t suddenly dry). “Feel any better?” 

“Much,” The word came out as a whisper. Castiel cleared his throat and took a step back. “Is that part of the package?” Castiel really hoped that Dean didn’t take offense and realized that he was just kidding. 

“Nah, that’ll cost you extra.” Dean smiled. Castiel gave one tentatively back. “Come on, we should get downstairs before your mom yells up at us.” Dean quickly found a button up flannel shirt in one of his bags. 

“You said this was informal tonight, right?” Dean started buttoning up the shirt in the mirror. 

“Right.” Castiel replied, realizing that he was watching Dean with intent. He looked over at Castiel and Castiel quickly looked out the window. 

The two walked out of the room and at the top of the stairs, Dean grabbed Castiel’s hand. Castiel’s eyes grew and Dean gave his hand a squeeze. 

“Look, I’m going to be doing stuff like this all weekend. You need to stop freaking out about it.” Castiel nodded. He knew that. Of course they needed to sell the fact that they were dating. 

They walked down the stairs and could hear Becky and Chuck in the kitchen. 

“…a man! I just…I don’t know how I…”

“Becky, he’s happy. Who cares?”

“He’s not Hannah.”

“And that’s a good thing. Now come on, they’re probably back down here.” Castiel pulled Dean’s arm back so they appeared to be still walking down the stairs. He also gave Dean a sympathetic smile. 

“I told you.” Dean shrugged, appearing not to be bothered by it. 

“I’ll just have to prove to her that I’m better for you.” Dean gave a crooked smile, only pulling the left corner up. Castiel cleared his throat and looked away as they reached the bottom of the stairs and Chuck and Becky came out of the kitchen. Becky had a tray of finger sandwiches and Chuck was holding a small plate of cookies. 

“Come in, sit down. We’re just waiting for Gabriel.” They both set down their plates as Dean and Castiel sat on the loveseat. Before Becky and Chuck sat down, the doorbell rang.   
“That’s probably Gabriel.” Chuck smiled and walked to the door. Castiel breathed a sigh of relief, although he wasn’t sure why. 

“Daddy! I’m home!” Yes, definitely Gabriel. There was a grunt form Chuck and then Chuck laughed. 

“Hello, Gabriel. Come in, Castiel and his date are here.” 

“Cassie!” Gabriel shouted as he ran through the house. Castiel stood up, bracing himself for his brother’s impact. Suddenly, a shorter man, with golden hair and eyes was running towards him. Gabriel ran into Castiel’s arms and jumped up, wrapping his arms and legs around Castiel’s middle. Castiel groaned at the sudden weight of his older brother. Gabriel laughed. “Still can carry me. Good for you. Now put me down so I can meet your new girl!” Dean had stood up as Gabriel untangled himself from Castiel. 

“Well, I’m certainly Castiel’s, and I am new, but I’m not a girl.” Dean and that smile (was it trademarked or something? If not, it should be. Castiel mentally shook that thought away) were offered to Gabriel. Gabriel had a reaction between his mother’s and his father’s. His eyes popped open as though he had never heard of anything so ludicrous in his life. 

“Oh. OOOOOH!” He exclaimed as he shook Dean’s hand. 

“Dean, this is my older brother Gabriel. Gabriel, this is my boyfriend,” there was that word again “Dean.” 

“I um…well, hi. I figured that I would’ve heard about this. How long have you two been together? The last time Cassie and I talked he wasn’t seeing anybody and that was just a couple weeks ago.” Gabriel shot daggers at his little brother. Castiel blushed. If there was going to be anybody that saw through this ruse it was going to be Gabriel. He could usually read Castiel like a book. 

“We weren’t ready for the family to know yet.” Dean replied, pulling Gabriel’s eyes back to him. “You know, it’s difficult trying to come to terms with something like this.” Gabriel narrowed his eyes at Dean, but seemed to buy it. He sat down on the giant L-shaped couch next to his mother. She smiled warmly at Gabriel. 

“Welcome home, honey.” She gave Gabriel a hug. “How’s California?” She asked when they broke apart. 

“Hot and bothered, but it’s where the work is.” 

“Work?” Dean asked, Castiel thought only to be polite. 

“Gabriel is an actor. He went to USC and got his degree for it. My mother originally went to the same school for the same reason, but changed her major to English where she met my dad first day of their sophomore year.” 

“So what kind of acting do you do?” Dean asked, looking at Gabriel quizzically. 

“Well, mostly plays. I love dramas, but comedies can be fun too.” Dean nodded, his eyes still narrowed before opening them back to normal. 

“You know, my younger brother would be disappointed with me staying in a house with a bunch of So. Cal. grads. He just graduated from Stanford. He’s in their law program now.” Castiel looked at Dean, trying to hide the surprising fact that he had a brother. They had spent so much time talking about Castiel and his family that they hadn’t touched on Dean’s. 

“As long as you didn’t go to Stanford, we’ll be fine.” Chuck winked. The room laughed. The five were eating some of the sandwiches and cookies when Becky glanced at the clock on the wall. 

“Oh! We should probably get going. Castiel, Dean, would you just want to follow us? We’ll take Gabriel and…”

“I want to ride with Cassie and his man-love!” Becky rolled her eyes. Castiel felt Dean’s hand on his kneed again, assuming that he had been bouncing it. Was it a nervous tick that he had never noticed before?

“Fine, let’s get going though. Drinks will start soon and you know how Joy gets.” They all stood and walked out the door.

**Notes for the Chapter:**

> Sorry this is a couple days late. Family things, the holidays, and sickness is not a good combo for a writer. Thanks to you all for the bookmarks, kudos, and comments!


	5. Chapter 5

Following the black Mustang that Castiel’s father had bought as a mid-life crisis car, Dean, Castiel, and Gabriel made their way through town. 

“I’m surprised you came, Gabriel.” Castiel turned around, hoping to keep the conversation on his brother and not his faux relationship. 

“What are you talking about? I love Bess!” 

“I know that, but I just didn’t know if you would be able to. I thought that you had a play.” 

“I’m only missing one performance and the understudy has been dying for a chance to get on stage.” 

“That’s good then, I suppose.”

“Enough about me, Cassie! You need to tell me how this happened.” Gabriel gestured between Dean and Castiel. 

“We met at a coffee shop.” Castiel blurted out, almost nervously. “I accidently spilled coffee on him and then he asked me out on a date.” Gabriel looked over Castiel’s face. 

“Uh huh. Well, that implies that you knew before that happened that you were interested in guys, so how did THAT happen?” 

“Oh.” Castiel went red. He hadn’t thought about that. Dean reached over and placed a hand on Castiel’s knee. Castiel looked over at him, but Dean didn’t turn his attention from the road. “I had been…thinking about it for years to be honest.” Castiel earned an encouraging squeeze from Dean. “I just hadn’t really acted on it, so when Dean proposed we go out on a date, I decided to actually do it and…here we are.”

“I just thought with Hannah,” Gabriel whispered, almost as if he didn’t want Castiel hear it. They hadn’t talked about her much since the engagement was broken off and Castiel had called Gabriel crying. 

“I just wanted a change, I suppose. And this one worked out for me.” Castiel smiled at Dean and then back to his brother. 

“Well, this is for sure a change. Everybody is going to lose their shit.” Gabriel leaned back, laughing. “Not that they’ll say anything. Have you met the fiancé?” Castiel shook his head. 

“No. I only know what he looks like from Facebook and that his name is Garth Fitzgerald IV. That’s…” Dean nearly slammed on the breaks. Castiel braced himself against the dashboard. 

“Sorry. I just…thought I saw something in the road.” Castiel glanced at Dean suspiciously. “Oh, it looks like we’re here.” Dean’s voice had lost that in control tone that it normally had and had a slight hint of hysterics to it. They followed the Mustang into a field beside a large, clearly fixed up barn. It had been painted. There were white Christmas lights and a banner hanging above the door. The banner read “CONGRATS BESS AND GARTH” in the wedding colors of navy blue and mint green. 

“Wow, Pastor Jim and Joy really went all out, huh?” 

“Of course. Bess is their only girl. Gabriel, why don’t you head inside? I think I need to prep Dean for everybody inside.” Dean didn’t protest. In fact, Dean’s face seemed to have lost some color as he stared at the banner.

“Do you mean Michael?” Gabriel waggled his eyebrows in a joking way. Castiel smiled to make it appears his brother was right. 

“Yes, I mean Michael.” 

“Good luck with that. I’ll be at the bar.” Gabriel slid out of the car and walked to his parents. They looked in the car as Gabriel appeared to be explaining to them what was happening. Once they went inside, Castiel turned to Dean. 

“What the hell was that? There was nothing in the road.” 

“What else do you know about the groom? Can you show me the pictures from Facebook?” Dean sounded the most nervous that Castiel had heard him. Castiel dug his phone out of his jeans’ pocket and pulled up his Facebook app. He found Bess’ page and showed him her profile picture, which was of the two of them. The remaining color in Dean’s face drained. 

“Shit. Shit, shit, fuck, shit.” 

“What?” 

“I went to high school with him. Not for long, mind you. I was only there for my some of my junior year, but still. He and I were lab partners. I…I don’t know what to do. I’ve never had this happen before.” Castiel saw actual fear in Dean. Something that he hadn’t expected to see the whole weekend. 

“Does he know what you do?” It was Castiel’s turn to appease Dean, so he was using a calm voice.

“No, I don’t think so.”

“Great. And do you think he’ll remember you?” Dean shrugged. “Okay, well then we’ll get in there and act like a couple, like nothing is different. If he remembers you then…well, we’ll cross that bridge when we get there.” Dean inhaled and exhaled deeply, and suddenly, the cocky Dean was back. 

“You’re right. I’m sorry. I just wasn’t prepared for that.” Dean smiled at Castiel. “Ready to go?” Castiel looked Dean over and then rested his eyes on Dean’s. 

“Are you?” 

“Always. Let’s do this.” Dean quickly got out of the car before Castiel could say anything else, so Castiel followed his lead. Dean waited for him near the front of the car. “Thank you, really, but I’m okay. Let’s go.” Dean offered his hand and Castiel took it, still skeptical about Dean being okay. Dean intertwined their fingers and the two began walking in. Castiel knew that the heart flutter was because of what was about to happen. 

Inside, the bar was decorated in the navy blue and mint and Christmas lights. It had clearly been swept out and scrubbed. There was a table up on a platform that had another banner on it that read “HEAD TABLE”. There was a bar off to the left with a bartender and more tables spread out for people to sit down and chat at. There wasn’t going to be food, but people were invited to stay until around 10. Castiel figured that his parents would want to stay for a long time. 

“This is a nice place.” Dean commented in Castiel’s ear. Castiel nodded. 

“They really must’ve been working on this for months. We should probably…”

“Hello, little brother.” Castiel would know that voice in his sleep. He turned to see his older brother Michael. He had blue/green eyes and dark hair. He was just about Castiel’s height. 

“Michael. How are you?” Castiel gave Michael a small smile. He had tried to keep Castiel in town when he wanted to leave after Hannah left him and once Castiel left, it had hurt their relationship. 

“Fine. How are you?” Michael’s eyes traveled to Dean. 

“I’m fine, thank you. This is my boyfriend, Dean. Dean, this is my older brother Michael.” Michael didn’t offer his hand, he simply nodded. Dean nodded back. 

“Nice to meet you. Castiel, care to grab a drink with me?” Castiel glanced at Dean and then back at Michael. 

“Sure, Dean, did you want something?” 

“I’ll just take a beer. Thanks, babe.” Dean smiled and squeezed Castiel’s hand before letting it go. That seemed to be his go to comforting gesture. Michael lead the way to the bar area where he order a neat scotch as Castiel ordered two beers. 

“So, why did you really bring that man here?” 

“He’s my boyfriend.” Michael laughed with no humor. 

“If it’s simply to make Hannah jealous, there’s no point.” Castiel stiffened. That wasn’t the point…was it? 

“I brought Dean because we have been dating for three months and I thought it would be time for him to meet my family. Apparently, I made the wrong choice.” Castiel replied coolly. 

“The rest of the family may have fallen for this, Castiel, but I don’t believe it for a minute.” Castiel shrugged as the bartender appeared with the beers for him. 

“Believe what you want, but…” Castiel turned and saw Gabriel and Dean talking, laughing. That couldn’t be good. “Excuse me, I have to go.” Castiel stuck a five-dollar bill in the tip jar, grabbed the beers, and quickly walked away, feeling his brother’s eyes on him the entire time. 

“…so he starts running around the living room with nothing on but…” 

“Okay! This story sounds like it needs to be stopped.” Castiel handed Dean his beer when he had straightened up from laughing. Castiel took a large drink from his bottle.   
“Oh come on, Cassie. This is the fun part of being a big brother. Getting to embarrass you!” Castiel sighed. 

“We still need to say hi to Bess and Garth. Excuse us.” Castiel grabbed Dean’s hand and pulled him towards a group of women that he assumed Bess was in the middle of. Half way there, they stopped, and Castiel glared at Dean. 

“What did I say about being alone with my brothers?” 

“Oh I’m sorry, was I just supposed to walk away from him? That would’ve been rude. You need to relax the grip a little bit. I know how to play the part and you need to trust me. Now, let’s meet the bride to be.” Castiel continued to glare at him, but they walked toward the group of women that had mostly broken up. There was a blonde sitting in the middle, gossiping with an older woman. 

“Excuse me, ladies?” Castiel spoke up. The blonde looked up and her eyes lit up. 

“Castiel!” She squealed and jumped up. She came around the table and wrapped him in a tight hug. “Oh, Castiel. I can’t believe you came! You look amazing.” She pulled away and took his free hand. “I am so so happy that you made it.” Bess gasped, as if remembering something. “Where’s your plus one!?” Castiel’s smile changed, at least to him it seemed more forced. Castiel gestured towards Dean. 

“This is my boyfriend, Dean.” The word had somehow become easier with each sip of beer. “Dean, this is my friend, Bess.” Bess looked between Dean and Castiel so quickly it almost looked like she was having a spasm. 

“Your what?! Castiel, this is your…?”

“Boyfriend, Dean.” Dean smiled that smile again and Castiel had to admit, the more that he saw it the more he actually liked it. 

“Wow, I…you…wow. Hi, welcome! Oh! You need to meet my soon to be husband! GARTH!” Bess shouted, loud enough for the barn to become quiet. A tall, skinny man with some stubble and short brown hair came walking from a group of men off to the side. 

“Hi, sweetheart.” Garth placed a kiss to the top of Bess’ head. 

“Garth, this is my friend, Castiel Novak and his boyfriend, Dean…I’m sorry, Dean, honey, what’s your last name?” Dean’s eyes were on Garth, almost daring him to repeat their past. Garth apparently didn’t notice. 

“It’s not Dean Winchester, is it?” Garth hadn’t even glanced at Castiel. Dean’s hand tightened around his beer. 

“Yeah, it is. Garth Fitzgerald, right?” Dean stuck his free hand out. They shook hands. 

“You two know each other?” Bess seemed just as surprised as Castiel pretended to be. 

“We went to high school together. Well, like what? A semester junior year?” Dean nodded, and then stepped back closer to Castiel. Garth shook his head and then smiled at Castiel. “Hey, man, I’m sorry. Just didn’t expect to see him here. I’m Garth, you’re Castiel, right?” The two shook hands. 

“Yes, nice to finally meet you.” 

“Same to you. Bess has been so excited since we got your RSVP. She really wanted to meet this plus one of yours. So, Dean, why don’t you come catch up with me? There are some people that you might remember from high school.” 

“Oh.” Dean looked at Castiel. “I just don’t know if I can leave Castiel...”

“Nonsense! Castiel and I need to catch up, too. Now you two go. Have fun. We’ll meet back up with you soon.” Dean widened his eyes at Castiel in a silent plea, but Castiel just smiled. Maybe he was being a little vindictive. Maybe he was trying to remind Dean to follow the rules and not be alone with his brothers. 

“Yeah, you guys have fun. We’ll see each other later.” Dean’s eyes were full of pure rage for a moment before they went back to normal. 

“Sounds good, baby.” Dean leaned in, gave Castiel a kiss on the cheek and then whispered in his ear. “You really don’t want to play this game with me, but it’s on.” Dean pulled away and then walked off with Garth. 

“Castiel, he’s freaking gorgeous! I need to know EVERYTHING! Now!” Bess pulled Castiel towards the table and forced him into a seat. Just as Bess opened her mouth to ask him a question, she closed her mouth at something over Castiel’s shoulder. Castiel turned around and was met with a pair of blue eyes and long, wavy, brown hair. 

“Castiel.”

“Hannah.”

**Notes for the Chapter:**

> As always, thank you guys so much for your bookmarks, reviews, and subs. I can't believe how many people are enjoying this. :) Love you guys.


	6. Chapter 6

Castiel and Hannah continued to stared at each other, neither saying a word. Castiel felt a sudden rush of affection towards her. Her eyes looked even bluer than he remembered them. 

“You’re looking well.” Hannah stepped closer to the table. 

“As are you.” Castiel replied. She gave him a gentle smile as she sat next to him. 

“Hannah, Castiel was just about to tell me about his boyfriend.” Bess stretched the word ‘boyfriend’, making Castiel uncomfortable. Hannah balked and blinked multiple times. 

“B…boyfriend? You have a boyfriend?” Castiel slowly nodded. At that point, Dean laughed loudly. It sounded so natural Castiel turned to see him. His head was thrown back at something Garth had apparently said. Castiel felt a small smile come to his lips, happy that Dean seemed to be enjoying himself. 

“That’s him.” Bess whispered. Castiel realized that the three of them had been watching Dean. 

“Wow, I…I’m very surprised. I thought…”

“Bess, sweetheart.” Becky had come up to the table. 

“Hi, Mrs. Novak.” Bess stood up and gave her a hug. 

“You look amazing. Tomorrow will be beautiful,” Becky turned towards Hannah and Castiel. “And just look at you two!” She beamed. 

“How are you, Mrs. Novak?” Hannah stood up to give Castiel’s mother a hug as well. 

“Great, sweetie, just great. Did you meet Castiel’s latest flame?” Becky narrowed her eyes in Dean’s reaction. 

“We haven’t met, but he was just about to tell us about him.” Hannah glanced over at Castiel. Castiel hurriedly finished his beer. 

“I need a refill. Anybody else?” The women didn’t respond before Castiel walked away from the table. He heard somebody follow him, but didn’t stop until he reached the bar. 

“I see your mother hasn’t given up on us.” Castiel spun around, finding Hannah there. 

“I think I could marry somebody else and she would still hold out hope for us.” Castiel replied. Hannah gave Castiel a sympathetic smile. 

“I’m sorry,” Hannah began, but was cut off. 

“Cassie!” Gabriel suddenly appeared at his brother’s side. “I need you.” Gabriel shot a look at Hannah. “You don’t mind if I steal him, right? I mean, you stole nearly eight years of his life.” Gabriel grabbed a whiskey glass and a beer off the bar, and then began leading Castiel away from the bar. 

“What the h*ll was that, Gabriel?” Castiel demanded when they were out of ear shot. 

“THAT,” Gabriel replied, “was me saving your sorry a$$ from getting sucked back into the Hannah Vortex.” Castiel grabbed the whiskey out of Gabriel’s hand. 

“I have no idea what you mean by that.” 

“I meeeeeeaN you have a gorgeous pile of man candy running around here and you’re hanging out with your ex at the bar. Dude, the Hannah shipped has sailed. Let her go.” Castiel downed Gabriel’s whiskey. 

“Maybe it hasn’t though.” Castiel practically whispered to himself. Gabriel, however, had heard it and his eyes grew wide. 

“No. No no no no no no. We are NOT going down that road.” 

“There was a ship and now there’s a road?” Castiel could feel the whiskey hitting him. He usually only drank beer. 

“Castiel,” a voice behind them spoke. Castiel rolled his eyes before turning towards his eldest brother. 

“Yes, Michael?” Michael narrowed his eyes. 

“Are you alright?”

“Just great, I’d be better if I had more whiskey.” Castiel pushed past Michael to get back to the bar. He looked around for Hannah, but apparently she had left already. Castiel sighed and put his empty glass on the bar. 

“Hey, you okay?” A soft whisper in his ear said. He looked up and saw green eyes filled with concern. Dean was very close. So close that Castiel could smell the beer on his breath. 

“Fine. Just…I’m fine.” Castiel decided not to burden Dean with all his problems. Dean would be able to leave all these issues at the end of the weekend, thousands of dollars richer for it. Why would he care about Castiel’s problems? He had been paid. All he had to do was enjoy himself for a free weekend. He wasn’t there to impress anybody. It wasn’t his brothers or parents that were telling him that he and his date weren’t good enough for the family. 

Dean frowned and looked at the bartender.

“Two whiskeys, neat please.” The bartender nodded and quickly produced two glasses of the amber liquid. Dean picked them both up and looked at Castiel. “Come on, let’s go for a walk.” 

Castiel hesitated, but decided to follow Dean. Dean led him outside and to his car. Dean leaned against the passenger side door and handed a whiskey to Castiel. He took it, but didn’t drink. He looked at Dean curiously. Dean took a sip from his own glass. 

“So, do you want to tell me what just happened or do you want to act like nothing did?” Castiel thought for a minute.

“I just…was thrown off by having seen her again.” Casteil replied as he leaned against the back door. 

“Yeah, you can prepare all you want, but nothing actually matches seeing an ex again.” Dean looked down and swirled his glass, as though thinking of a similar situation. “I don’t think you ever told me about what happened with the two of you.” Dean looked at Castiel through his lashes. Castiel stared for a moment. The look on Dean’s face was one that Castiel couldn’t quite identify. It was somewhere between interest and slight fear that he’d crossed a line. He looked…beautiful. Castiel shook that thought from his head. It had to be the whiskey. Castiel took a drink before taking a deep breath. 

“Hannah and I dated for a long time. Most of high school and all of college. I proposed and she accepted. We were living together and mostly happy. Then we started fighting.” Castiel paused, trying to gauge if Dean was listening or even interested. 

“About what?” Dean offered softly. 

“Oh everything. She would get mad over the food I left in the fridge a day after it expired and that would make me snap at her for not making the bed and then it was suddenly about how I never do things for her. How I didn’t help her plan the wedding even though whenever I tried she would either reject my ideas or ignore them entirely. Then she yelled that I didn’t even want to get married and slammed the door to our bedroom. Of course, I thought she was being ridiculous. I still wanted to get married, but that night, I was tired of the fighting so I let it go. I figured I would come home from work the next day and we’d apologize, say we were sorry, and move on. I slept on the couch, got up, went to work the next day, came home and she was gone. All of her things too. Found a note that said she couldn’t do this anymore. I tried to go to her mom’s house and talk to her but…” Castiel felt the tears come to his eyes, not even meaning for them too. It still hurt. After all that he had done to try and make them work, and she was willing to just let go so quickly. 

“Hey,” Dean put his hand on Castiel’s shoulder. Castiel looked at him. “That wasn’t your fault.” Castiel stared into Dean’s eyes. He seemed like he truly cared about Castiel. This wasn’t an act. This appeared to be the real thing. 

“Thank you,” Castiel replied. He had an urge to lean in and kiss those incredibly plush lips. Castiel wasn’t sure if he was imagining it, but he could’ve sworn that he saw Dean’s eyes flicker to his lips before Castiel felt his phone vibrate in his pocket. 

“Oh, sorry, just a moment.” Dean took a step back and cleared his throat. 

“Yeah, yeah, take your time, man.” Dean downed the rest of his whiskey. “I’ll be inside.” Dean quickly walked away as Castiel answered his phone. 

“Castiel Novak.” 

“Castiel Novak, this is Charlene Bradbury. I am calling to inquire how your weekend is going.” Castiel laughed loudly. He was sure the whiskey was really hitting him. 

“Well hi, Charlie.” 

“Are you going to answer my inquiry?” Charlie didn’t drop the professional tone in her voice. 

“It’s going…” Castiel looked around, making sure there was nobody else around. “He was a bit of an ass on the way up here and to be honest I was debating on calling the whole thing off, but he’s really turned around and he’s been great with my family.” 

“Aw, that’s great! How’s everything else going?” 

“Great, actually. And nobody suspects a thing. Except for Michael, but he’s also an assbutt, so…” Charlie laughed. 

“Oh, Castiel, have you been drinking?” 

“No, what makes you think that?” 

“You only talk like that when you’ve been drinking.” 

“I have no idea what you mean. But he’s just so…”

“Castiel!” Somebody called from the barn door. 

“Oh, Charlie, I’ll call you tomorrow. I have to go.” 

“Wait! He’s so what?!” 

“I really have to go, Char. I’ll call you tomorrow.” Castiel hung up his phone when he saw Garth appear. 

“Hey, Dean was wondering where you ran off to and I needed some fresh air.” Garth looked around. “What were you doing out here?” 

“Oh, a friend from Chicago called me and she just wanted to know how the weekend was going.” Castiel wasn’t sure why, but he was actually comfortable around Garth, even though they had just met. 

“Good, good.” Garth took a deep breath and looked at Castiel. “There’s another reason I came out here.”

“Oh?”

“Yes, Bess wanted me to come ask you if you would want to go out for drinks with her and some of her bridesmaids.” Castiel’s eyes must’ve widened, because Garth laughed. 

“You don’t have to if you don’t want to, she just wants to know.”

“I’ll come in and talk to her.” Garth simply nodded and turned to leave. Castiel followed, thinking how he was going to tell Bess that he wasn’t going to go out. He just wanted to go home and sleep. Things were going well with Dean, but he didn’t want to push it too hard and have everything come crumbling down. 

As the two of them walked in the barn, Castiel looked around for Dean. Why couldn’t he find him? Castiel walked over to Bess, still with Garth. 

“Castiel!” Bess stood up and took his hands with both of hers. “We’re going to that one place where we went after we all graduated?”

“Cupid’s Bow? I don’t know…”

“Oh pleeeeeease?! Come on! It’s my wedding weekend. It’ll be so much fun.” Castiel still didn’t want to go, but Bess seemed too excited for Castiel to tell her no. 

“Okay. Okay, we can go. I just need to grab Dean.” Bess clapped her hands excitedly. 

“YAY! Okay, go grab him. I think Garth might be taking his guys out, so maybe Dean could go with them! That would be so fun!” Castiel just gave Bess a smile before turning to find Dean again. 

“Did you happen to see where Dean went?” Bess looked around and bit her lip, then shook her head. Castiel frowned and then walked away to try and find Dean. Then, he heard him laughing again. He was starting to get used to that sound. Not only used to it, but he was beginning to like it. Castiel turned to see Dean and Gabriel at the bar. Castiel walked over and placed his hand on Dean’s shoulder. Dean turned around and smiled. 

“Hey, babe.” Dean gave Castiel a kiss on the cheek. Castiel smiled back. “Who was on the phone?”

“Charlie.” Dean just nodded, and Castiel was thankful that he didn’t do anything to blow their cover. Although, that was what Castiel had paid for. Castiel felt like he had to keep reminding himself that this was a business transaction. Maybe he wouldn’t be feeling so weird about the situation if he remembered that. 

“So, I hear that Bess wants to go out drinking?” Dean smiled and took a sip from his glass. 

“She does, and I think that I’m going to go.”

“Is that so?” Dean smiled wider. “Because Garth invited me out with him and his friends, but I was wondering if you would want to just go home.” Castiel considered telling Bess that he had changed his mind, and that he and Dean were just going to go back to his parents’ house and go to bed. However, he did want to make sure that Bess was happy. 

“That should be fun. We can see each other at home.” 

“Okay, you two need to stop.” Gabriel took a big drink of his own. “Your eye-fucking needs to stop now. And I swear to God if I hear you two tonight…”

“Shut up,” Dean joked. The three of them talked at the bar until there were just a few people left in the barn. Castiel’s parents had gone home almost thirty minutes before, when Garth and Bess walked over. 

“Everybody ready?” Bess clapped again. 

“I’ll drive.” Dean offered. The group, about three for Bess and three for Garth, walked outside. Once at their cars, Bess and Garth gave each other kisses. Dean put his hands on Castiel’s hips and pulled him close to whisper in his ear. 

“I’ll see you later.” He pulled back and gave him a kiss, this time on his lips. Castiel felt like the breath had gotten knocked out of him. His whole head seemed to be swimming with Dean. His lips, his smell, even his hands at his hips. Castiel wanted more, but just as he was about to take it further, Dean pulled away with a smile. 

“Alright, you two. Let’s get going!” Garth called. Castiel’s head was still spinning when Bess grabbed him and pulled him towards her car. 

“You two can finish that when you get back to your parents.” Castiel slowly nodded. 

“I suppose your right.”

**Notes for the Chapter:**

> I am SO sorry this is so late. My brother surprised us all and came home for Christmas, so we've been doing family stuff! However, as a Christmas/Hanukkah present, I am going to upload the next chapter on Saturday! And, as always, thank you SO much for your reviews, subscriptions, and bookmarks! You guys are amazing.


	7. Chapter 7

Dean looked around the bar, still trying to figure out how he had gotten there. Yes, he was in Wisconsin because of work, but why had he agreed to go out with guys from high school that he barely even remembered. He was sure he had classes with some of them at some point, but other than Garth, he had to be reintroduced. He supposed it was so that Castiel could go out and have a good time without having to worry about him. 

Castiel. Dean thought. He was…an interesting character. More interesting than most of the people that Dean…accompanied to high school reunions, funerals, even Mothers’ Day celebrations. This had been his first wedding though. There was just something about Castiel that made Dean say yes. He’d been next to Meg at her desk when he’d called and heard his voice. It was gruff and deep and there was still a hint of innocence. There was something there that sounded like hope. Hope that maybe things would get better with this weekend. 

Then when he saw him? Dean knew he was done for. He had sex hair, and blue eyes that made the sky seem dull. Dean knew that this weekend, if he could make it happen, he’d be giving Castiel certain things that he would normally charge extra for. 

“So, Dean, what is that you do now?” A guy that had been in Dean’s Algebra asked. 

“I’m a mechanic.” Dean responded naturally. That was his go to. Sometimes he was a writer, sometimes a banker, but the mechanic one wasn’t technically a lie. He partly owned a garage with his uncle just outside of Chicago. 

“You were always good at shop. I remember that.” The guy responded as he took a drink of his beer. Garth had disappeared with two other guys, but Dean was content sitting at the bar. 

“Yeah, it’s a pretty good living.” The two continued to make small talk until Garth came back up. He was clearly pretty drunk and was going to need help getting home. 

“Dean, we all wanna know. How’d ya end up with a stiff like Castiel? I mean, weren’t you like THE ladies’ man in high school? How’d ya…ya know?” Dean smiled and chuckled to himself, sipping at his whiskey before answering. 

“Well, we met at a coffee shop. I was sitting down in my usual chair, just taking the fifteen minutes before I head to the shop to have to myself.” Dean suddenly saw it in his mind’s eye, as if it had really happened that way. “I noticed him when he came in, but didn’t want to say anything. You know? It’s kinda weird to just hit on somebody.” Dean looked around and noticed that not just the wedding party was listening to him, but some of the bar patrons. “So, I was sort of watching him, pretending not to, and then I noticed him coming closer and closer until I suddenly saw that he was practically on top of me,” Dean tried not to picture Castiel literally on top of him, “and then I felt hot coffee in my lap.” Everybody gasped, but Dean laughed. “He turned so red and was so apologetic that I felt a little bad for him. He told me he would pay for dry-cleaning and this and that and then I told him that wouldn’t be necessary if he would go out on a date with me. Well that just made him blush more and he stuttered out a yes and here we are.” Dean didn’t even need to remember to smile. He had been smiling the whole time. When had he started feeling like that? When had the fake backstory become so perfect that Dean could picture it as though it had actually happened? And when in the hell did Dean WANT it to be real?

“Wow, look at you, man. You almost look as love struck as Garth here.” A man Dean didn’t know, but was pretty sure his name was Russ, slapped Garth on the back. Dean chuckled and finished off his whiskey. 

“I wouldn’t go that far, but maybe someday. Garth, buddy,” Dean slid Garth’s arms around his shoulders, “let’s get you home.” Garth looked like he wanted to nod, but he threw up instead. 

Breakbreakbreakbreakbreakbreakbreakbreakbreakbreakbreakbreakbreakbreakbreakbreakbreak

Castiel bought another round of shots at the bar and brought them over to the table. 

“Yay! Thank you, honey!” Bess exclaimed. She grabbed a glass and waited for everybody else to hold them up. 

“To Bess and Garth,” One of the bridesmaids smiled. Everybody echoed here and threw back the drinks. 

“Okay, now!” Bess turned towards Castiel. “You need to tell us more about Dean.” 

“Like what?” Castiel asked. He knew that he was probably not going to remember most of this tomorrow. 

“Well, what does he do?”

“How did you meet?” One woman asked. 

“Where can I get one?” Another asked, earning her giggles from some of the other girls. 

“Dean is a mechanic.” Castiel thought back to him talking about the car and figured that Dean knew enough about cars to pass as a mechanic. 

“Are you sure?” Bess narrowed her eyes. 

“Wh…what do you mean? Of course I am.” 

“Well I need to move to Chicago because all the mechanics around here are ugly and have a beer gut.” Bess and the girls laughed. Castiel laughed too, but it was mostly to let out nervous energy. 

“We met at a coffee shop. He was sitting in a chair when I walked in,” Castiel thought he should add some details. “I noticed he was in jeans and he was…well you’ve seen him. Gorgeous.” Castiel could see Dean sitting in the morning light streaming in, hitting Dean’s hair as he read the paper and drank coffee. And for some reason, not at some café. He was seeing Dean with bed head, in a t-shirt and boxers at the bar in his kitchen. Castiel tried to chase that thought away. Dean wouldn’t want that with somebody like Castiel. However, the thought stayed in Castiel’s mind as he continued. “I was watching him more than where I was going and I dropped my coffee all over him. I, of course, started blushing and apologizing profusely. He smiled at me and laughed it off, saying I could make it up to him with a date. I was so flustered that I agreed and I almost forgot to get his information.” Bess was smiling wide and the other girls were grinning too. “What?”

“Nothing. It’s just, great to see you so happy again.” 

“Do I seem happy?” Castiel asked. Bess nodded vigorously. 

“Castiel, I’ve known you for a long time, but I think that this is happiest I’ve seen you. You seem lighter even. You…I’m just so happy for you. And that kiss you two had before you left?” Castiel blushed. “Seriously, I almost feel bad for Gabriel when you get home. Almost.” Bess laughed. 

“I wouldn’t. Do you know how much I heard when I was in high school?” Castiel and Bess laughed, enjoying the rest of the night. Castiel kept taking shots and was drinking beers. He knew that he wasn’t exactly sober when the night ended. In fact, he was feeling so good, he walked out to the ATM just outside the bar and withdrew money from his savings.

At the end of the night, one of the girls that hadn’t been drinking, drove everybody home. Castiel was dropped off at the same time Dean’s black car came pulling into the drive way. 

“Good night, Castiel. Don’t you dare be late to my wedding!” Bess called as Castiel shut the door. 

“Well hi there.” Dean smiled as he got out of the car. Castiel walked over, grabbed Dean by his shirt and pulled him in for a kiss.

**Notes for the Chapter:**

> Merry Christmas and Happy Hanukkah! Here is my gift to you all! And you all have given me enough with your subscriptions, kudos, and reviews. Love you guys. Thank you guys so much and enjoy the holidays! PS- sorry it's so short!


	8. Chapter 8

Dean’s hands slid to Castiel’s hips as he accepted the kiss. Castiel gently swiped his tongue along Dean’s bottom lip, making Dean groan and Castiel’s tongue made its way inside Dean’s mouth. Castiel could taste the whiskey, and something else he wasn’t quite sure what, but he didn’t care. He couldn’t believe that he was actually doing this, but in his drunken state, he was willing to admit to himself that he’d wanted this, wanted DEAN, practically since he laid eyes on the man.

Dean pinned Castiel against the door of the Impala with his hips and ran his hands up into Castiel’s hair, making it messier than it was even coming back from the bar. Castiel slipped his arms around Dean’s waist as Dean’s lips traced down Castiel’s jaw and along his neck. It was Castiel’s turn to groan when Dean found and sucked on his pulse spot.   
“Maybe we should move this inside.” Dean suggested. Castiel nodded, feeling Dean through his jeans. Castiel grabbed one of Dean’s hands and led him to the porch. Castiel slowly and quietly opened the door, hoping nobody would be awake. As he looked around, Dean put his hands on Castiel’s hips, pulled him back into him, and was placing kisses to the back and side of Castiel’s neck. Castiel closed his eyes, forgetting his place. Those lips really knew what they were doing. 

“Upstairs?” Dean whispered, his breath hot in Castiel’s ear. Castiel shook his head and made Dean follow him to the stairs that led to the basement. If Dean was confused, he didn’t protest as Castiel opened the door and the two made their way down the stairs, with their hands roaming each other’s bodies. 

“There’s a spare bedroom down here that’s much more private. I figured it would be better than having Gabriel making comments tomorrow.” Castiel whispered in the dark, his hand sliding through Dean’s belt loops to pull him closer. Dean just nodded as Castiel opened the door to the bedroom, pulling them both inside. Dean’s lips attacked Castiel’s before he could even kick the door shut. Dean and Castiel’s tongues danced inside their mouths, each exploring the others with passion. Castiel grabbed Dean by his shirt again, this time to throw him on to the bed. Castiel straddled Dean’s hips and could feel Dean’s length through his jeans. 

“Having a good time, Mr. Winchester?” Castiel whispered before pressing his lips to Dean’s nose, cheek, and finally his neck. Dean hummed. 

“Very.” Was all Dean responded before he flipped over and had Castiel on his back. Castiel gasped, but Dean took that opportunity to steal Castiel’s mouth for a kiss. He slowly began to unbutton Castiel’s shirt, taking his time so that Castiel could change his mind at any time. Castiel never did. As Dean reached the last button, Castiel began to unbutton Dean’s shirt, with more difficulty. Dean chuckled, making Castiel begin to giggle as well. 

“Need some help?” Dean offered. 

“Please?” Dean unbuttoned his shirt and took it off. Castiel stared at him with intent, not wanting to miss a single second of it. However, once Dean’s flannel was off, there was another obstacle. The damn black t-shirt he’d been wearing when he arrived at Castiel’s. Castiel pulled at it, making sure that Dean understood that he was to take that off too. Dean shook his head. 

“It’s only fair that we have the same amount of clothes on,” Dean teased. Castiel pouted, but then Dean leaned down and took his protruding bottom lip between his teeth, making Castiel forget what he was mad about. Dean sucked on Castiel’s bottom lip, and Castiel pulled Dean closer to him, making their lips touch. Castiel pulled at Dean’s shirt again, and Dean allowed him, raising his arms up and breaking their kiss for a moment, then attaching them again. Castiel turned the tables on Dean so he could properly take in the man. Castiel had expected Dean to be in good shape, but actually seeing him was a completely different situation. 

His chest was large and strong with muscle. His mid-section was hard and defined too. It should’ve been a crime to keep that under a shirt. Castiel leaned down and took one of Dean’s nipples in his mouth, earning him a deep growl like sound from Dean that Castiel could feel radiating in his chest. 

“You like that?” Dean made the noise again when Castiel swirled his tongue around it. 

“Cas,” Dean whispered gently, making Castiel knit his eyebrows together and look up at him. Nobody but family had ever given him a nickname, and the way Dean said it was almost more intimate than the act they were doing. “Come back up here.” Castiel nodded and made himself level with Dean, before once more finding himself on his back. Dean was ripping off his undershirt and then kissing him just as passionately as before. Castiel reached down and unbuttoned Dean’s jeans, which Dean returned the favor. Castiel groaned into Dean’s mouth when he felt his erection freed from the denim. Dean moaned back and rutted Castiel and Castiel felt like he might blow. 

“D…Dean!” Castiel called, not caring who heard. Dean stopped at looked at Castiel. “N…now?” Dean’s eyes widened, but he nodded. 

“I…shit. I don’t have anything down here.” 

“Then go get them.” Dean simply nodded and slipped his shirt on before running upstairs. Castiel was thinking of Dean’s mouth on him in multiple places, making him leak precum. He couldn’t wait for Dean to come back and…

“Got it.” Dean was breathing heavy, but Castiel wasn’t sure if that was about the running up and down the stairs or something else. He shed his shirt once more and crawled his way towards Castiel with his hands filled. One with a condom and the other had a small bottle of lube. He set them down and slid Castiel’s undershirt off, kissing him again. Castiel kissed him back. Dean slid his hand inside Castiel boxers, taking his hard, leaking erection in his hand. Castiel moaned louder than he had previously. 

“Sh, we can’t wake up the whole house, now can we?” Dean whispered in Castiel’s ear, grazing it with his teeth. Castiel bit his bottom lip to keep from another moan escaping him. “Now how would you like to do this?” Dean gave Castiel a gentle squeeze. Castiel exhaled sharply. 

“You. Just…you.” Castiel breathed out. Dean slid Castiel’s boxers off and then his own. Castiel took in Dean’s cock. It was standing fully erect and long. Castiel wasn’t sure if he could handle it, but he was going to try. He also knew that Dean was going to take care of him and make sure that he was okay and safe. Castiel wasn’t sure why he knew that, but he knew it. Dean seemed so caring and was moving with Castiel so slowly so that if he needed to, Castiel could back out, but Castiel wasn’t going to. He wanted to do this and he wanted to be with Dean. 

“Turn over.” Dean demanded. Castiel complied, and he heard Dean gasp. 

“What?” Castiel felt Dean’s lips at his back, tracing what he knew was there. His wings. He’d gotten large, black, feathery angel wings tattooed down to his lower back that he’d gotten as soon as he moved to Chicago. “Oh those.” 

“Later.” Dean replied, continuing his lips around Castiel’s wings and then down to his lower back. “Are you sure about this?” 

“Yes!” Castiel practically shouted. Dean lathered his hand in lube, and gently circled around Castiel’s entrance. Castiel sighed deeply, hoping that Dean would hurry up. Dean, as if reading his mind, softly pushed his index finger in barely. Castiel whined. “Dean! Mmmm.” Castiel wanted more. He was surprised how good and right all of this felt. Castiel felt himself adjust just as Dean slid his finger up to his second knuckle. “Oooh!” Castiel could feel it more, especially as Dean began to move his finger and out of him. Castiel could feel himself leaking more when Dean slid his whole finger inside. “Yeeeessss.” Castiel hissed, knowing feeling like he might lose it soon without Dean actually being inside him. Dean thrust his second finger in, moving his fingers quicker and spreading them out, to make Castiel open himself up. Then Dean hit Castiel’s prostate. Castiel let out a cry that he hadn’t expected. Dean hit it again and Castiel made the same noise. “Dean, I…I’m so close.” Castiel whispered. He didn’t trust his voice not to crack at that moment.   
“Ready?” Dean asked as he applied more lube around Castiel’s entrance and then opened and slid the condom on. 

“Please.” Castiel answered quietly. He knew that he wouldn’t last long with Dean, but he was ready for it. Dean lined himself up and Castiel felt the head of Dean’s erection touch and then slowly come inside him. Dean inched his way as Castiel felt himself stretch in ways he didn’t think were possible. It hurt, but it also felt better than Castiel believed it would. 

Dean reached around and began stroking Castiel, making him lean back into Dean. It only took a few strokes for Castiel to lose his load on the comforter. Dean wasn’t far behind, a few more strokes and he came, moaning out a “Cas” before falling on top of Castiel. He and Castiel were breathing deeply and Dean placed a kiss to Castiel’s temple before sitting up, and slowly pulling himself out. 

“Bathroom?” 

“Across the hall.” Castiel breathed out, hoping Dean heard him. Dean got off the bed and walked out of the room. Castiel was still trying to catch his breath when Dean came back with a towel. 

“Want to get cleaned up?” Dean offered the towel to Castiel and Castiel greatly took it. He wiped up his legs and the comforter and then fell back against the pillows. Dean laid next to him. 

“That um…that was…”

“Was that okay? I know you’ve never done anything like that before and I just got excited, so if it was too fast…” Castiel gave Dean a gentle kiss. 

“Yeah, it was more than okay. It was great. I…I’ve never…not even with Hannah…” Dean wrapped his arms around Castiel and pulled him into his chest. Castiel laid his head down and listened to Dean’s heartbeat. 

“Why’d you get the wings?” Dean asked as he traced when Castiel knew one of the feathers was. 

“A couple reasons. I told you my brothers and I were all named after angels, so Gabriel and I always talked about getting tattoos with wings, and Gabriel got his when he moved out to California and I decided to get them when I moved to Chicago. They represent freedom too. The freedom that I got from moving away from Hannah and getting to a new big city.” 

“My brother and I always talked about getting matching tattoos, too. Maybe we could when he comes home from law school.” 

“Your brother means a lot to you, doesn’t he?” Castiel could feel sleep so close. The alcohol, the long drive, and sex had made him exhausted. He closed his eyes. 

“Yeah, he does. We can talk more in the morning. You get some shut eye.” Castiel yawned and nodded. 

“In the morning.” Castiel could hear Dean humming a song. “What’s that?” 

“Hey Jude. My mom used to hum it for me.” Castiel felt himself drift to sleep with Dean’s humming in his ear. Dean felt his eyes close too, not noticing when he fell asleep.   
Dean woke up, still in the dark. He wasn’t sure what time it was, but he knew that Castiel was still asleep on his chest. He wasn’t sure why, but it made him happy. He was thinking that maybe this thing with Castiel would work out. Maybe he could get out of this life and work at the garage with Bobby full time. He and Castiel could actually date and live together in the future. He wouldn’t have to lie to people about what he did. 

Dean didn’t want Castiel to wake up, but he had to go to the bathroom, so he gently moved Castiel off of him (and Castiel made a small mewing noise of protest) and then stood up. He tripped over Castiel’s jeans and saw Castiel’s wallet skip across the floor. Dean sighed and walked to pick it up. Now, Dean wasn’t one to judge, but he realized that Castiel’s wallet was thick. He also noticed a receipt that said that Castiel had taken nearly four thousand dollars out of his savings account. 

Had Castiel planned this? The whole night? Getting drunk so he could act like he didn’t know what he was doing and could experiment with a guy? Well fuck that. If Castiel wanted this to be some experiment, then it would cost him more than that. God, Dean was so stupid. He’d actually started caring about him and thinking that maybe things would get better for him. Dean should’ve known better. People were always just going to see him as the hired fuck doll. Dean quickly grabbed his clothes and went into the bathroom. He got dressed, hoping the tears in his eyes wouldn’t actually fall.

**Notes for the Chapter:**

> Hope everybody's holidays went (or are going) well! Thank you guys so so much for your subscriptions, kudos, and reviews. You are all amazing! Love you guys!


	9. Chapter 9

Castiel woke up to a dark room, alone. His exposed skin was covered in dried sweat, and he was slightly confused. Why was he in the guestroom in the basement? The last thing he really remembered was kissing Dean and then leaving the barn with Bess. Had he been so drunk he decided not to even try and wake Dean…

Dean. The night (and a pounding headache) came rushing to him in a blur. Drinking with Bess and her friends, coming home to see Dean get out of his car, and then…had they kissed? Surely not. Surely that had been a drunken dream. ‘Drunk actions are sober thoughts’ a voice in the back of Castiel’s mind quoted to him. ‘What a stupid saying’ Castiel thought back. And if he’d only dreamed the kiss, why had it felt so real? Even in a drunken state, kissing Dean seemed real. The feel of his plush lips, the way his strong hips had pinned Castiel to the car, the tender touches Dean had used to take things so slow. It had been a very vivid dream, Castiel concluded. There was no possible way it was real.  
Castiel looked around the room and saw his clothes strew about as though they’d been torn off him by somebody else. ‘I was drunk’ Castiel told himself. Most people that are drunk don’t take their clothes off properly. He decided not to wake the rest of the house (the clock on the bed showed that it was only ten after seven o’clock), and take a shower downstairs in the basement. He could collect his thoughts before facing everybody. Castiel gathered his clothes and slipped into the bathroom.   
In the shower, Castiel ran through the night’s events again, this time with more clarity. He and Dean HAD kissed before leaving with their separate parties, that was for certain. That kiss had….well, it apparently had been enough to cause Castiel to have dreams about the man. Vivid dreams. Vivid dreams in which Castiel had never been touched, or kissed, or treated like that before. Was there something behind the kiss? No, surely not. Dean had just been doing his job. That’s what Dean had been paid to do. Kiss Castiel. Dean wouldn’t be attracted to a man like Castiel. Dean also probably didn’t want to be tied down in his line of work. This was going to be over tomorrow and Castiel would go about his life. Find himself a girl and Dean would find another paying woman or man or…Castiel stopped and grabbed the generic shampoo his parents always left down here “just in case” and massaged it into his hair as he pushed the thought of Dean with somebody else out of his mind. Not because it bothered him, but because it was simply none of his business. It wasn’t. He knew that. After today, Dean would be more than free and welcome to date whomever he wished. And Castiel would have no say in the matter. Why did that thought fill him with an odd feeling of dread? Why did the idea of picturing Dean with somebody else make him want to beg Dean not to do it? Castiel could just picture some beautiful blonde woman taking Dean out to her high school reunion and Dean would lay on the charm. Asking her why she thought she couldn’t get her own date. Asking her if she’d like to get to know each other better. Taking her to his place. Castiel shook the thought from his head. It was NONE OF HIS BUSINESS. Why did he need to keep telling himself that? 

Castiel turned the water off and got out of the shower. He dried himself off and wrapped himself in a towel. He needed to talk to Dean. He would get dressed and come clean about the dream. If he didn’t. he would be acting different around him all day and Dean would figure it out anyway. Dean was very good at picking up on people’s emotions. Castiel grabbed his clothes, and began walking upstairs. Thankfully, he didn’t run into anybody, and got to his room without an incident. Inside his room, was a different story.   
Dean was laying on top of the covers, only in his boxers. He was fast asleep, at least appeared that way, and Castiel’s breath caught in his throat. He knew that this was real, and had a feeling of déjà vu seeing Dean like that. No, it had only been a dream. Castiel quickly grabbed his clothes and was about to run to the bathroom to change, when he heard Dean. 

“Leaving so soon?” Dean’s voice was rough with sleep and his eyes weren’t even opened yet, but Castiel knew that he was awake. 

“I…I was just…um…” Castile cleared his throat. “Going to get dressed. In the bathroom.” Castiel continued to stand there awkwardly. “Um…bye.” Castiel walked as fast and quietly as he could to the bathroom. He threw on a t-shirt and jeans, waiting to put on his suit until it was closer to the time of the ceremony. He was hoping that Dean would be dressed when he walked into the room, but wasn’t sure if he would be. Castiel walked back to the room and opened it, seeing Dean rifling through his bag, still only in his boxers. 

Dean turned around and saw Castiel staring. 

“Well come in, it’s not like you haven’t seen it before.” Castiel looked out into the hallway, trying to see if there was somebody behind him that Dean was saying that for. It didn’t appear as though anyone else was around, but Gabriel was just across the hall. If he was awake and heard Dean say something contrary to the idea that they had been together, things could get messy. Castiel knew that he wasn’t made for this fake relationship thing. He walked into the room and closed the door. 

“You look…well.” Castiel didn’t know what else to say. This was going to be bad. 

“Thanks?” Dean shot a funny look over at him. Castiel shook his head. 

“Sorry, I just…after last night….” Dean paused and looked into Castiel’s eyes. Castiel gulped. Apparently, that hadn’t been the right thing to say. Dean’s green eyes looked hurt, and a little sad, before he blinked and it was gone. 

“Look, don’t worry about last night. I…”

“I was drunk and I must’ve thought I’d wake you up. I’m sorry if I freaked you out by possibly leaving you with my family.” Dean paused, a look of confusion passing his face before realization dawned on him. Castiel watched Dean open his mouth and then close it a couple times before Dean laughed, humorlessly, and shook his head. 

“You think…okay. Yeah, no, it’s fine, man. Thanks for being considerate.” It was Castiel’s turn to be confused. 

“What do you mean ‘You think’?” Dean shrugged himself into a t-shirt. 

“Nothing, just a long night. Ready for some breakfast?” Dean slipped his jeans on and pushed past Castiel out the door. Castiel watched him and then followed once Dean had gotten to the stairs. 

Dean, however, wasn’t sure what to do. He had thought about charging Castiel for last night, but if he didn’t even remember it, what could he do? He didn’t want to freak the guy out. ‘He’s just a customer’ a voice said to Dean, but Dean knew that the voice was wrong. ‘He’s not just any customer’. He knew that the moment he heard the phone call between Castiel and Meg. He knew that the moment he met him. This guy was different from his other clients. So, if Castiel needed to think nothing happened for his own sanity, then so be it. Far be it from Dean to change that for him. 

Down in the kitchen, Castiel grabbed bread to put in the toaster. 

“Need help?” Dean offered. He wasn’t planning on it down the stairs, but he figured he didn’t need to act like a dick the whole day. 

“If you could just make the coffee, that would be great.” Castiel gave Dean a gentle smile. 

“Where is it?” Castiel nodded at the cupboard next to himself and went back to the toaster. He turned and was met with Dean’s chest. Dean looked at Castiel with that stupid smile. The smile that would probably haunt Castiel long after this weekend was over. “Found it.” Dean whispered. Castiel just nodded and stopped trying to count the freckles that danced across Dean’s face. Dean moved and Castiel went to the refrigerator. He looked and saw jars of different things that one could put on toast. 

“Jelly, jam, or preserves?” 

“Uh…I literally didn’t know those were different things.” 

“Of course they are.” A voice from the staircase said. Dean and Castiel turned to look and saw Chuck there. He was in a robe, with a t-shirt on it that said something about a deadline. “The preserves are actually made by a family friend. Let’s go with those, son.” Castiel nodded and grabbed the jar from the refrigerator. “You’ve got some things to learn if you’re going to be a part of this family.” Castiel felt a blush come to his cheeks, and a sense of guilt because he knew the truth. 

“I’d be happy to learn, sir.” Dean smiled at Chuck, but Castiel thought it looked a little different. A little sad, but that couldn’t be it. It must’ve been his hungover brain. 

“After coffee. Did you two figure out the maker okay?” Chuck eyed the coffee maker on the counter as though it might sprout legs and run away. 

“Oh yeah, I’ve got the same one at home. I can’t go more than an hour without my morning coffee.” Chuck smiled. 

“Ah, a boy after my own heart.” Chuck glanced between Castiel and Dean. “Well, maybe not mine.” Chuck gave a knowing grin. “I didn’t hear the two of you come in last night. Have fun out and about did you?” 

“Oh yeah,” Castiel jumped in, hoping that Dean wouldn’t even answer. “Bess and her friends were a lot of fun.” 

“Good, good, and you, Dean?” Dean nodded as he grabbed five coffee mugs out of the cupboard. 

“Yes, sir. I hadn’t seen some of those guys in a long time so it was nice catching up.” Chuck seemed satisfied and changed the subject. He began making eggs when Becky and Gabriel came down the stairs. 

“Aw, boys, you didn’t have to.” She smiled, even at Dean, and then looked to Gabriel. “And why aren’t you helping them?” Gabriel thought for a moment before smirking. 

“Well, I’m already the favorite, so why not give Cassie a chance to take my title? Not that he will.” Gabriel walked to the coffee maker and poured himself a cup as Chuck laughed. “Mom?” Gabriel held up the remaining empty cup. 

“Yes, please.” Gabriel poured the last of the coffee into her cup and slid it to her spot at the kitchen island. Becky took a sip and looked around. “So, Gabriel, before we leave for the wedding, I want you to clean up the kitchen since your father, Castiel, and Dean cooked breakfast.” Gabriel’s mouth dropped and then he stuck his tongue out at Castiel. 

“Fine, but I think Cassie and I are going to take Dean to all our old hangouts.” Castiel choked on the piece of toast he was eating. 

“Oh, we are?” Castiel coughed out. 

“Yup! Dean and I were actually talking about it last night.” Dean had actually forgotten that, but now that Gabriel had mentioned it, it was somewhere in there. A vague conversation about seeing the city that his ‘boyfriend’ had grown up in. In reality, Dean didn’t want to do that. Dean wanted to stay home and stay under the covers and not have to pretend for once. However, that wouldn’t work. 

“I’d love to. I mean, you talk about this place all the time, Cas. I’d love to see some of it.” Castiel heard that nickname, but didn’t comment. It made him think of last night and how intense his dream had been. 

“You won’t be late to the wedding, will you?” Becky worried her lip between her teeth. 

“Mom, the wedding doesn’t start until 6, we’ll be fine.” Gabriel rolled his eyes for dramatics. 

“Okay, well, after we eat and Gabriel cleans up, we can do that.” Castiel smiled and Dean smiled back, not sure what else to do.

**Notes for the Chapter:**

> Happy New Year, everyone! Let's hope 2017 is the best one yet! Hope you all had a fun and safe New Year's Eve and Day. And, as always, thank you so much for your comments, subscriptions, and kudos! Love you, guys!


	10. Chapter 10

Castiel watched in distrust as he watched Gabriel pack the dishwasher incorrectly.

“Gabriel, how is it that you live on your own?” Gabriel looked up at Castiel with a pout. 

“For your information, Cassie, I get along just fine without anybody else’s input.” Castiel rolled his eyes, but Dean nudged Castiel with his elbow. 

“Leave the man alone. He’s doing his best.” Gabriel smiled at Dean and then looked at Castiel. 

“I like him. You should keep him.” Castiel looked over at Dean and gave him a fond, half smile. 

“Yeah, I like him, too.” Castiel watched Dean give him the smile that he’d grown so attached to. Castiel didn’t focus on the last part of Gabriel’s words because he knew that would hurt. It would hurt tomorrow going home and when his parents called him in the next week or so, he’d have to pretend that he and Dean had just broken up. 

“That’s so nice, Cas. I wish I could say the same.” 

“Oh ha ha.” Castiel gave Dean a gentle push to his shoulder.

“Alright, if you two are going to act like this I’ll let you go around town yourselves.” The two looked over at Gabriel. 

“What do you mean?” 

“All googly eyed and mushy.” 

“We promise, let’s go though. Your mom will be upset if we’re late.” Dean stood up and Castiel followed. 

“Great! I’ll go change and then we can go.” Gabriel ran up the stairs. Dean looked anywhere but Castiel. It was suddenly weird without the rest of the family there and Castiel not remembering. How did he not remember? Maybe Dean was losing his…ability. Castiel suddenly looked uncomfortable. 

“You alright, man?” Dean asked. 

“I’m just…did I fall down last night when I was drunk? My legs are just...sore.” Dean tried not to laugh. Yeah, most guys were the next day after the first time. This wasn’t the first time Dean had taken another man’s virginity (with a man, anyway), but it was the first time he was pretty happy with himself for it. The first time that he wanted to do it again. The first time that Dean really had enjoyed himself. What the hell was wrong with him? 

“No, maybe you fell down the stairs or something.” Castiel was confused. He kept getting snippets of last night in flashbacks, but he knew that it was a dream. It was fuzzy and hard to recall if they were actual memories. But Dean would’ve said something. Something about them…being together. He hadn’t. Of course Dean would’ve said something so that he could get paid. He wouldn’t have just been with Castiel because he wanted to. People like that usually weren’t drawn to Castiel. Castiel was about to ask him something else about last night, but then Gabriel came bounding down the stairs. He was pulling on a shirt and Dean noticed a pair of golden wings on the inside of his arm. 

“So there are your wings.” Dean said matter-of-factly. Gabriel smiled at them. 

“Yeah, I didn’t get ones all down my back like somebody. Did he tell you he got them by himself?” 

“You got yours by yourself too!” Castiel huffed.

“Yeah, but my tattoo isn’t all down my back! Anybody can get a little one like this done alone. Yours are freaking huge.” Gabriel continued to babble about the tattoos. Castiel knew that he was just jealous that he didn’t think of getting them down his back. “…black. Much like his soul.” Gabriel stuck his tongue out. 

“Are you trying to tell me you think your soul is golden?” 

“Duh. I’m named after an ARCH-angel. They all had golden wings.” 

“I’m fairly certain that you’re wrong, but we need to get going since you two came up with this ludicrous idea to show Dean around town. You know it’s only going to take about an hour? Maybe less.” 

“Cassie, if you don’t want to go, by all means stay. I can show Dean-o a good time by myself.” The way Gabriel said that, almost insinuating that something might happen if he let them go alone, made Castiel angry for no reason. He only had a short time left with Dean, and he was going to spend that time all with Dean. No matter how much it was going to hurt to say good-bye tomorrow back in Chicago. 

“No, let’s go.”

“Great! Dean, my man, you’re going to drive and I’ll just randomly point and shout directions at you.” Gabriel then turned on his heel to led the trio outside. 

“Hard to believe he’s actually an adult, huh?” Castiel bumped Dean. Dean gave him a little half shrug and followed Gabriel outside. Castiel thought that was odd, but chalked it up to the long night and then walked out to the already warm day. 

“So, I’m thinking we could start at the high school, and then we could show him Fish Lake, and…” Gabriel was still babbling as Dean unlocked the Impala and Gabriel climbed into the backseat. 

“How are we going to get into the high school? It’s the middle of July. Nobody’s going to be there, not even summer school is still in session.”

“How would you know? You’ve never done summer school.” Castiel rolled his eyes as Dean started the car. 

“No, but you did, and until my freshman year of high school, Mom never let me stay home when she went to get you. I hated it.” 

“Oh yeah, Dean?” Dean glanced at Gabriel in the review mirror. “Take a left out of the driveway.” Dean nodded and followed Gabriel’s directions (between his arguments with Castiel) before pulling into the high school parking lot. “Okay. Here it is. Cassie and I spent a combined eight years here.” 

“Well, there was one year that we were here for the same time.” Castiel stared at the building. He was overcome with nostalgia. Here was where he’d met Hannah, but now he couldn’t think of why he’d been drawn to her. Maybe it had been meeting Dean, but now it didn’t seem important. 

“Whatever, come on. Let’s go.” 

“Go where? We already talked about this, nobody…” 

“To the football field!” 

“Why the hell would we go to the football field?” Castiel frowned at his brother. “None of us played football.” 

“I know, but the football field is where the janitors meet and they’ll let us in.” Gabriel got out of the car and started walking. 

“We better go, or he’ll just come right back.” Castiel looked over at Dean. Dean was staring out the windshield. 

“Yeah, lets go.” Dean quickly got out of the car, leaving Castiel to wonder what was going on. Castiel followed Dean out and they walked together after Gabriel.   
Dean wasn’t meaning to be rude, but he knew what had happened here. He knew this was where Castiel had fallen in love with Hannah. He didn’t want to be here. He was trying not to let it bother him, but he couldn’t help it. He and Castiel would never have a past like that. He and Castiel weren’t anything. This was a simple business transaction for both of them. They would be done with each other after they got back to Chicago. Dean hated himself for falling for this guy. He was also pretty pissed at Castiel for forgetting (or pretending) to forget that they had had sex the night before. ‘There was no way he’s pretending,’ Dean thought. ‘He would be freaking out if he really thought that happened.’ Dean sighed to himself as he climbed up the hill to see four men in navy blue jumpsuits smoking cigarettes talking to Gabriel. Castiel had caught up with him at this point, and Dean grabbed his hand. Castiel seemed to jump slightly, but he relaxed and even intertwined his fingers with Dean’s. Dean gave Castiel a gentle smile, and the two walked up to the group. 

“...show his boyfriend inside.” Gabriel seemed to be arguing with one of the men. 

“Come on, kid. You know I could lose my job for that.” The guy took a drag from his cigarette before throwing it on the ground and stomping it out. 

“Gabriel, really, it’s fine. We can just go to Memory Park.” 

“Yeah, man. I’ve seen enough high schools in my time.” Gabriel glared at the men but then sighed heavily. 

“Fine.” Gabriel turned around and started walking down the hill, the other two in tow. “You’ve got a reunion coming up soon anyway, don’t ya, Cassie?” Gabriel asked as they made it to the bottom of the hill. 

“Oh,” Castiel replied, nearly forgetting about it. “I suppose I do.” It had been nearly ten years since he graduated high school. He hadn’t attended his fifth-year reunion because his break up with Hannah was still too fresh for him to come back. 

“And you’ll bring Dean back for that, right?” Dean squeezed Castiel’s hand in a comforting way. Just another thing about the man that he had grown used to. He liked that Dean just made the smallest of gestures to make sure that he was okay. Or asking in a way. Castiel squeezed back and looked into Dean’s eyes. 

“If Dean would like to come, I would be happy for Dean to come back with me.” Dean smiled his heart-melting smile and Castiel returned it. He was surprised how much he meant that. He really did want Dean to come back with him. He wanted to bring Dean back and show him off to the people who hadn’t come back for the wedding. Castiel knew that it was stupid, and he knew that Dean would most definitely not be coming back with him, but for right now, he could at least pretend. 

“I would love to, Cas.” Dean brought Castiel’s hand to his lips and gave it a kiss. 

“Okay, see, this is why I should’ve let you two go off on your own.” Gabriel leaned against the Impala. 

“Why?” Dean released Castiel’s hand and let him walk around the other side of the car. 

“Because, you two are all mushy and gross. Now let’s go to the lake.” The three got in the car and took off again. Gabriel giving directions without arguing with Castiel this time.   
Once at Memory Lake Park, the three got out and Gabriel took a deep breath. 

“There’s not a lot of open space in L.A. This is nice.” 

“I agree with you. The city is nice and all, but I grew up between South Dakota and Kansas.” Dean looked around the lake. “I love stuff like this.” 

“You grew up in the country, but moved to the city and you’re a mechanic, why?” Gabriel asked as they started walking around the lake. 

“Well, my brother was in law school and my dad passed away. There was nothing tying me there anymore. My Uncle Bobby had moved to Chicago with his wife Ellen after Ellen’s daughter Jo decided to go to Northwestern, so I followed him out there. He gave me a job, and the rest, as they say, is history.” Dean wasn’t sure when Castiel had grabbed his hand, but he felt a squeeze. He looked over and Castiel had a small smile on his face. Dean realized that Castiel didn’t know anything about him. Dean knew nearly everything about Castiel and now he was going to start telling him things so that maybe, just maybe, it wouldn’t be such a permeant good-bye when they went home. 

They were about half way around the lake when Castiel suddenly stopped and looked at a tree. Dean was pulled back gently, but Gabriel continued to walk, not noticing the other two. 

“What?” Castiel was still looking at the tree before he took a deep breath and looked at Dean. 

“This is stupid. It happened so many years ago.” Dean was confused. 

“What did?” Castiel nodded at the tree. 

“That’s where I kissed Hannah for the first time.” Dean looked at the tree, and then back to Castiel. Castiel was looking at it, but Dean had decided something. Dean cupped Castiel’s face in his hands and placed a kiss on his lips. Castiel seemed surprised at first, but then the wrapped his arms around Dean’s neck and kissed him back. It wasn’t didn’t feel like the one they had shared the night before. It felt comforting. Like Dean was just making sure that Castiel was still doing okay. Suddenly, there was somebody clearing their throat. The two broke apart and Gabriel had his arms crossed. 

“Really?” Was all he said. Dean shrugged and Gabriel threw his hands up. 

“We can go home if you two don’t want to do this.” 

“No, Gabriel, it’s just…this is where I first kissed Hannah.” Castiel replied, sheepishly. 

“And I wanted to help take those bad memories away.” Dean offered. Gabriel chuckled slightly. 

“Well, I guess I can’t argue with that. But come on, I’ve got to show you where Cassie and I had our first swimming lesson and he nearly drowned.” 

“Why is that funny?” The trio then made their trip around the lake, with Gabriel and Castiel giving little stories about what had happened at certain parts. Dean was really enjoying himself. After they had circled the lake twice, Gabriel looked at his phone. 

“Oh man, we better get home. It’s nearly two! Only four hours until the wedding and we’ve so much to do!” Gabriel declared dramatically. The other two laughed. 

“You’re right, Mom will get mad. We really better get going.” Castiel, Dean, and Gabriel walked back to the car and drove back to the Novak’s to get dressed for the wedding.

**Notes for the Chapter:**

> Hey guys! Sorry this is late, but I will be uploading another chapter today so that I get back on track! As always, thank you guys SO much for your bookmarks, kudos, and comments! Love you all!


	11. Chapter 11

Dean, Castiel, and Gabriel arrived back at the Novak's just after two o'clock. They walked inside, and walked into the kitchen, seeing Becky and Chuck making lunch. 

"Oh, hello, boys." Becky smiled at them. Castiel wasn't sure if his mother was just pretending to be nice or had finally come around to Dean being a part of his life. Even if was just for the weekend. Castiel shook himself mentally. He HAD to keep reminding himself that this wasn't real. Dean wasn't really his boyfriend. Dean was going to leave and not talk to Castiel sometime in the next twenty-four to forty-eight hours. 

"I grilled some chicken breasts if you'd like some." Chuck nodded towards the plate on the island of the kitchen.   
"Don't eat too much, though. Jim and Joy would never let us live it down if you don't eat your food. Now, we'll need to leave for the church around five to get a good seat. Everybody in town is going to be there, so everybody needs to be ready to go by four forty-five. Is that clear?" Becky glared at the men in her kitchen, as if daring them to contradict her in anyway. 

"Four forty-five sounds great." Dean smiled, using his charm. He was hoping that if Becky saw him and Castiel dressed up and dancing and having a good time at the wedding and reception, she would be happy for Castiel and accept his next partner, even if it wasn't Hannah. 

"Good, now you all eat and then go get ready. I'll be in the shower." Becky walked out of the kitchen and up the stairs. Chuck soon followed her as the other three ate. Once Gabriel was done, he too went upstairs and left Castiel and Dean alone for nearly the first time all day. Castiel wasn't going to mention that. He wanted to say something to Dean.

"Dean?" Castiel offered. Dean turned his green eyes towards Castiel and Castiel was still trying to get used that look that Dean gave you when you held all of his attention. It was focused, but soft. Castiel cleared his throat. "I just wanted to say thank you for this weekend. I know that...we might not have a lot of...alone time from the wedding until we leave, and I may forget to tell you, but I just wanted to say thank you for putting up with my family and everything else." 

"Cas, you...you don't have to thank me." Dean replied, still not taking his eyes off of Castiel. "I just..." Just what? Just am happy that you're happy? Am glad I could be of service? "am having a great time getting to know you and your family better." There. That seemed very middle of the road. Castiel gave Dean a warm smile and picked up his empty plate, placed it on top of his own and walked them over the sink. Castiel began washing them, and Dean watched him. Imagining Castiel doing that on a Saturday afternoon after a late breakfast because the two had been out late the night before. Dean stood up, walked over, and wrapped his arms around Castiel's waist. Castiel froze for a moment, before relaxing and leaning back into Dean's chest while he finished cleaning the dishes. Dean had an impulse, and he thought about fighting it, but what the hell? He wasn't going to be seeing this guy much longer anyway.

Dean leaned down and pressed his lips to Castiel's neck. Castiel gave a small gasp in surprise. What the hell was Dean doing? Did he think that somebody was watching them? Dean continued moving his lips around Castiel's neck, and Castiel didn't make him stop. He even tilted his head so that Dean had better access. Dean gently drug his teeth along Castiel's pulse point, drawing a sigh from Castiel. 

"Dean," Castiel whispered. "If you don't stop, we won't have time to get ready for the wedding." Castiel didn't care if whoever was watching them heard that or not. He really didn't want Dean to stop, but they really had to get ready for the wedding. 

"We've got plenty of time, Cas." Dean whispered in Castiel's ear before biting his earlobe, making Castiel shudder. 

"D...Dean, really." But Castiel's protests fell on deaf ears. Dean moved his hands to Castiel's hips and pulled him back just slightly so that there was no more room between them. 

"Want to go upstairs?" Castiel didn't know why, but he nodded. Dean led them upstairs and into Castiel's room. Dean hadn't expected this. He had thought that Castiel would push him away completely and that would be the end of it. He would have his answer and he could get through the rest of the weekend professionally. That, evidently, was not going to be the case. 

Once the two of them were in Castiel's room, Castiel wrapped his arms around Dean and pulled him into a kiss. This kiss started as the one by the lake: soft, and sweet, and gentle. However, it quickly turned into something more. Dean had his hands on Castiel's hips and pulled him closer again. Castiel began to back up until his legs hit his bed and he fell down, bringing Dean with him. Neither of them broke the kiss, and Castiel slid one of his hands into Dean's hair. Dean kissed the side of Castiel's mouth before kissing his jaw and down to his neck once again.   
"Damn it, Cas." Dean whispered against Castiel's skin. Castiel wasn't sure if he'd done something wrong, or it was just another one of those things about Dean. Right now, he didn't really care which one it was as long as Dean's lips were on him in some way. Castiel began to gently guide Dean's head back up to his when a knock came to the door. 

"Son of a bitch." Dean huffed before rolling off of Castiel and sitting on the edge of the bed. Castiel sat up quickly and cleared his throat. 

"Come in!" Castiel hollered in a voice he hoped didn't sound too rough. The door opened and Gabriel walked inside, his hair wet. He was wearing a t-shirt and shorts. 

"I just got out of the shower if anybody needs to take one." Gabriel looked between the two of them and smirked. "Sorry, it appears that I've interrupted something." Castiel opened his mouth to argue, but Dean beat him to it. 

"Yeah, you're such a cockblock." Castiel felt himself turn bright red at that comment, but it appeared to appease Gabriel because he held up his hands. 

"Sorry, my bad. I'll...be going." Gabriel then quickly retreated from the room, shutting the door with a loud 'bang'. Castiel looked over at Dean. 

"You really shouldn't have said that." Dean knitted his eyebrows together at Castiel. 

"What do you mean?" 

"I mean Gabriel's got a big mouth. He's going to tell my parents what you said." Dean waved a hand at Castiel, as though he was being ridiculous. 

"No, he won't, and if he does, who cares? We're supposed to be boyfriends, remember? Boyfriends do that kind of stuff." Castiel glared for a moment before replying. 

"Yes, REAL boyfriends do that kind of stuff." Dean stared at Castiel, hard. That had hurt. He didn't know why, but it did. Why had the word real hurt him so much? Damn it, it was because he was starting to catch feelings. It was because he was starting to think that maybe, down in the kitchen, Castiel had actually liked him and now he knew the truth. This wasn't going to go anywhere. Dean was just fooling himself. 

"Yeah, I guess you're right. And we're not REAL boyfriends, are we? If we were, things would be a hell of a lot different. Like you might actually know something about me." Dean spat. Castiel seemed taken aback. What the hell was that about? Was Dean really trying to make him feel guilty about that? 

"Well who knows. You've got so many walls up, nobody knows who you really are. Do you actually have a brother that goes to Stanford law? Do you really have an Uncle Bobby? I mean, Dean, you can't even tell people what you actually do for a living." That was it. He could take abuse about himself all day. Hell, he told himself stupid shit like that on a daily basis, but coming after his family? After Sammy, and Bobby, and Ellen, and Jo? Fuck that. Dean wasn't going to let that slide. He should say something about that. About why he had so many walls up and why felt the need to lie all the time, but instead, Dean was going to run away. 

"Fuck you, man." Dean grabbed a change of clothes and stormed out of the room, leaving Castiel to think about the harsh words he had said. 

"Fuck." Castiel whispered to himself when he heard the water turn on in the bathroom. 'Great job, Castiel. He really hates you now. He was actually acting like he wanted you. Maybe you two could've talked about being together after getting back to Chicago, but no. You screwed that up.' Castiel ran his fingers through his hair and groaned. What the hell was he going to do now?

Dean turned the water on in the shower and waited for it to heat up. The thought about Castiel and how pissed he was. Where the hell did the guy get off about telling him what about his life was true and what wasn't? He was one that had hired Dean to lie to his whole fucking family for a weekend. And DEAN was the one with the trust and lying issues? He who lives in glass houses and all that bullshit. Yes, Dean has walls up. Everybody has walls up. Nobody exposes themselves wholly after knowing a person for two whole days! Who the hell did Castiel think he was? 

Back in his room, Castiel's phone was ringing in his pocket. He looked at the caller ID again, and saw that it was Charlie. He sighed and answered it. 

"Hello, Charlie."

"'Hello'?! You tell me that you're going to call me back today, it's nearly three there, I know the wedding starts at six, and all I get is a hello?!" Castiel scrubbed his hand down his face. 

"Sorry, how are you? How's Comic Con?" 

"Oh fine. Dorothy and I were first in line for Hall H today! We waited here for...how long, babe?" Castiel heard Dorothy say something, but couldn't quite hear her. "A long time. I don't need to bore you with this. YOU need to tell ME what's going on with your stud." 

"My stud?"

"Yeah! Have you guys kissed at all? Is he nice? Is he attractive?" Castiel heard Dorothy again, but this time Charlie laughed. "Of course I wouldn't be attracted TO him, but that doesn't mean that Castiel isn't, or that I can't find him good looking. Anyway, can you answer any of those?" 

"He...he is very attractive, and he's been nice for the most part. He has put up with my mother comparing him to Hannah, so that's good."

"Thumbs down from Mom, but how's your dad handling it? And your brothers? I mean, I know it's fake, but having their support through your fake coming out might help strengthen your relationships later on." 

"Gabriel and my father don't care. Michael I only saw last night and he, of course, didn't approve. The only real issue I think my mother has is that he's not Hannah, but I think she's starting to come around to it."

"That's good. This seems like it's working out."

"Charlie, I think I'm really attracted to him. Is that bad?" Charlie began to laugh. 

"Honey, you're asking your gay best friend if it’s okay that you're gay. Yes, yes, Castiel, it is okay to be gay." 

"That's not the part that I'm worried about. It's his...occupation that worries me."

"Oh. Well, maybe talk to him and see how that goes. Maybe...maybe he likes you back. Maybe he thinks you're dreamy. Maybe...something must've happened because a woman in the crowd screamed something. "Oh shit! Here they come! Castiel, I gotta go, but just go for it. Tonight either at the reception or after, just tell him how you feel! Love you! Enjoy yourself!" Castiel heard Dorothy again. 

"Bye, Castiel!" 

"Bye, love you guys." Castiel didn't get a response to that besides the beeping showing the call had been ended. Castiel laid back in his bed and then heard another knock at his door. He sat up and saw his mother walk in. 

“Castiel! What are you doing? You haven’t gotten in the shower yet?” 

“Well, no. Dean is in there now and…” 

“Well go use the one in the basement!”

“I already took a shower…” 

“Go! Now! I will not be late!”

“Mom…” Becky began clapping so that Castiel stood up. “Okay, okay!” Castiel quickly grabbed his suit and brought it down to the bathroom. He sighed and started the shower once again.

**Notes for the Chapter:**

> Here it is! Thank you guys with your subscriptions, kudos, and comments! You guys are the best and I love you!


	12. Chapter 12

Castiel walked into his room and saw that Dean wasn’t there. He wasn’t sure if he was relieved or upset, but he knew that that meant Dean was somewhere else in the house, possibly talking to Gabriel, which could be bad. They needed to talk, and Castiel knew that, but he also knew they had time on the way home. He got dressed in his suit, and began tying his tie when there was a knock at his door. 

“Come in!” Gabriel walked in and leaned against Castiel’s door jam. He was wearing khaki pants and a short sleeved collared shirt. Castiel felt slightly over dressed, but he figured since he was closer to Bess, he should be more dressed up. 

“So, I’m really sorry that I cockblocked…”

“Will you stop saying that?” 

“You’re still a prude, huh?” Gabriel grinned cheekily. “Seriously, Dean is downstairs and he seems a little upset, so if I made you guys upset, I’m sorry.”

“Don’t worry about it. Is the bathroom free?” Gabriel stared at Castiel, not answering. “What?” Castiel snapped.

“Nothing, I just…you two suddenly seem so weird. I just feel like it’s my fault, and I’m sorry.” Castiel closed his eyes, sighed, and then looked at his brother. 

“Gabriel, don’t feel bad. Seriously, Dean and I will get past this. Can you go tell Dean I’ll be right down and then we can talk?” Gabriel still eyed his brother, but nodded and then left the room. Castiel was going to fix his tie in the bathroom, but he supposed he should talk to Dean. He grabbed his jacket before walking down stairs. He heard his mother talking about who was all going to be at the wedding and who would be together at the reception. He really didn’t care. He had thought he would care about Hannah and if she was bringing someone, but now he didn’t. He’d decided that he wanted to be with Dean. They would make it work. Couples fought, and he had said some stupid things, but they had time to talk things out on the way home. They just had to make it there. They had to make it through tonight and then tomorrow morning and then they could lay everything out. 

“Cas,” Castiel jumped at Dean’s voice, not realizing that he had reached the bottom of the stairs. He took Dean in. He didn’t have a tie on, but he had a white button up shirt and black pants. His sleeves were rolled up. “Your tie is backwards.” Dean’s voice was gentle. Like he was the one that had said something hurtful. Castiel looked down and noticed the tags from his tie blue sticking out. He sighed. 

“You would think with as often as I wear ties…” Castiel began to untie it (and noticed Dean lick his lips). 

“Let me help.” Dean reached out and slowly tied Castiel’s tie. Castiel looked around to make sure none of his family was in earshot. He knew that he would never hear the end of this if one of them heard him apologizing. 

“Dean, I…I just wanted to apologize for what I said. I didn’t mean to hurt your feelings and…” 

“No chick-flick moments.” Dean’s eyes were fixed on the tie. He finished and smoothed it down, and then met Castiel’s eyes. “But thank you.” Dean flashed a smile that Castiel couldn’t help but return. Dean grabbed Castiel’s tie and pulled him into a kiss. Castiel kissed him back before there was somebody clearing their throat. Castiel pulled away and saw his father with his arms folded, but a sly smile on his face. 

“Sorry to intrude, but it’s almost time to leave.” 

“Thanks, Chuck.” Castiel could’ve sworn he saw a blush come to Dean’s face, but that couldn’t be. Dean should have been used to being caught like that. Hazard of the job, right? Castiel felt guilty for that thought. The two really needed to talk. 

Chuck smiled and then walked back into the kitchen with the rest of the family. 

“Ready?” Dean whispered. 

“As I’ll ever be.” Castiel replied as Dean slid his hand into Castiel’s and led them into the kitchen. Becky looked at the two of them and smiled. 

“Don’t you two look handsome together.” 

“Thank you, Becky.” Dean smiled back. “So, you were telling us about who couldn’t make it to the wedding?” 

“Honey,” Chuck interrupted after Becky opened her mouth to reply. “I think we need to get going. Boys, are you ready? Who’s driving?” 

“I think I’ll drive tonight.” Gabriel replied. He had his rental, but he hadn’t driven since he had been home. 

“Okay, Dean? Castiel?” Castiel felt Dean squeeze his hand. He enjoyed that feeling. Dean giving him a small comforting gesture. Castiel hoped this is what Dean had meant. 

“I think we’ll drive ourselves, too. We’ll meet everybody at the church, if that’s okay.” 

“Of course! Whoever gets there first needs to save seats for everybody else, alright?” Becky eyed Dean and Castiel, as though they would be so late that she and Chuck would have to save their seats until the ceremony started. 

“Why don’t we all just follow each other? That way we know that we’ll make it at the same time.” Chuck suggested. 

“Yeah, that’s a good idea. Let’s get going.” Becky grabbed her purse off the countertop and led all of them outside and into their respective cars. Once again, Dean and Castiel were alone in the car. 

“So, I know you said no chick-flick moments, whatever that means. But, I truly am sorry for what I said. I never should have said anything like that, and I…”

“Okay, chick-flick moments means something like this. Where you apologize for hurting my feelings. You don’t need to. I know things got a little…tense, but we’re passed it. We need to get though tonight and then tomorrow and then we’ll get to go home.” Dean gave Castiel a smile. “We’ll have a good time tonight and tomorrow morning and then we can annoy each other all the way back to Chicago.” Castiel chuckled to himself. 

“I think I can deal with that.” 

“Great. Let’s get going.” Dean started the Impala and backed out of the driveway. He waited for Becky and Chuck to pull in front of them, and then followed them. Gabriel followed them, making faces at the two of them the whole way to the church. 

Once there, they all parked, and walked into the church together. Becky was not wrong. The church was already packed with people, and it was difficult to find room in the pew that they all could fit in. They found one near the middle of the church and took their seats. The room filled so that there were no more seats and at exactly six o’clock, the music began. Garth walked down with a woman that Castiel was sure was his mother, followed by a man that looked incredibly like Garth. They gave him hugs and then sat down. Garth walked back to the vestibule and then walked Joy down the aisle. She gave him a kiss on the cheek and then Garth stood up next to the preacher. He looked nervous. 

“I’ll bet you two drinks tonight that Garth cries. He’s always been a crier.” Dean whispered in Castiel’s ear. Castiel bit his lip to keep from laughing. 

“You know it’s an open bar, right?” Dean shrugged and the two laughed quietly. Castiel felt an elbow in his ribs. He looked to his mother who glared and then put her fingers to his lips. Castiel nodded and then turned back to Dean. Dean smiled and Castiel smiled back. The music changed, and the groomsmen and the bridesmaids were walking down the aisle. Castiel watched a man come down with another girl, and then, he saw Hannah. She looked beautiful. Her dark curls were pinned up and her dress was a deep blue, strapless gown that reached the floor. Castiel felt Dean grab his hand and give it a squeeze before intertwining their fingers. He was happy that Dean was there with him. He supposed that he could make it through the weekend on his own, but it was so much nicer to have somebody there with him. The feeling of Dean’s hand in his made him feel like he was actually holding on to something.   
The music changed once more and the congregation stood up and saw Bess and Jim at the end of the aisle. They smiled at each other and it looked like Bess had already been crying. Dean had nudged Castiel and, when Castiel looked at him, nodded towards Garth. Castiel glanced over and Garth already had tears flowing down his cheeks. 

“Two whiskeys, neat.” Dean whispered before giving Castiel a kiss on his temple. Bess and Jim walked down the aisle together. Jim handed Bess to Garth, and shook Garth’s hand. Then he walked and sat down next to Joy. Garth and Bess stared at each other throughout the ceremony. Castiel couldn’t help but feel happy for her. She looked beautiful in her dress, and was practically glowing from happiness. Dean rubbed circles on Castiel’s hand throughout the ceremony. It was actually something that Castiel wasn’t sure Dean knew he was doing. Before too long, the pastor was pronouncing them man and wife and they shared a kiss. Everybody clapped and the ran down the aisle, together. The groomsmen and the bridesmaids followed them. 

“Well, that was nice, wasn’t it?” Becky wiped her eyes. Chuck wrapped an arm around her waist. 

“You’re actually a big softie, aren’t you?” 

“Oh stop.” Becky swatted at Chuck’s hand good naturedly. “We should get to the barn. It should be a lot of fun.” 

The group left again. They arrived at the barn at nearly the same time. Gabriel walked over and threw an arm around Castiel. 

“Cassie, let’s get drunk and you can watch me hit on your old classmates.” Castiel rolled his eyes, but allowed his brother to lead him into the bar. He could hear Dean laughing quietly to himself. They all found a table for themselves and they all talked. 

“Cas, I think I’ll take the whiskey now.” Dean smiled. 

“You owe him a whiskey?” 

“Yeah, he bet me two drinks that Garth would cry.” The table laughed and Castiel and Gabriel stood up to go get drinks at the bar. 

“Castiel,” Gabriel began as they waited in line. 

“Whoa, this must be serious.” Castiel joked. 

“It is. You know, I’ve given you a lot of crap this weekend, but you seem…lighter. That’s a weird way to say it. You always seemed down about Hannah, but you’ve been smiling all weekend. You and Dean seem like you’re in love.” Castiel looked over at the table and saw Dean smiling and laughing with his parents. He wouldn’t say love. He knew that he was feeling something for Dean, but it was far too early to be in love, but yeah, there was something. 

“Well, I don’t know in love, but I do like him. A lot.” 

“Well good. I’m happy for you, bro.” Gabriel thumped Castiel on the back and then they ordered their drinks and waited for them. 

“Oh, shit. I think Michael is headed to the table.” Castiel spun around and watched his eldest brother walk to the table that the rest of the family was seated at. 

“Great.” Castiel mumbled under his breath. He knew where this was going to go. Gabriel and Castiel got their drinks and walked back to the table. 

“Hello, brothers.” Michael smiled up at them. He was sitting right next to Dean. Dean looked irritated. 

“Michael.” Gabriel and Castiel replied as they handed out drinks. 

“We were just discussing your relationship, Castiel.” Michael leered. 

“What about it?” Castiel growled. 

“Different things about it. You met in a coffee shop, right? And what else? You two aren’t living together?” 

“No, we’ve been dating for three months. Most people don’t move in with each other after three months.”

“Well, if you say so. I just think it’s so odd that now all of a sudden you’re gay and…”

“Michael,” Chuck spoke up. “Stop it right now. Your brother is happy. You need to leave him alone.” Castiel looked up at his father, shocked at the hard tone in his voice. Michael looked at his father. His mouth was in a hard line, but he nodded. 

“Yes, sir. I think I see some friends. I’ll see you all later.” Michael stood up and left.

“Thank you, Dad.” Castiel was still in shock that his father had just said that to Michael. 

“Of course, son.” The two shared a smile. 

The wedding party arrived and the party truly began. They ate, drank, and when the DJ started, Gabriel dragged Castiel out to the dancefloor. Two songs later, a slow song began and Castiel began to walk off, but he was cut off. Hannah was standing in front of him. She smiled. 

“Hello, Castiel.”

“Hello, Hannah.”

“Recognize this song?” Castiel listened for a moment before he really heard it. 

“I do. We danced to this at prom our senior year.” Hannah offered her hand. 

“For old times’ sake?” Castiel was hesitant. He glanced over and saw that Dean was laughing with Gabriel. Castiel took her hand and the two began to dance. 

Dean was nursing his third whiskey. He had quickly drunk the first two, but wasn’t trying to get drunk tonight. He wanted to enjoy his night with Castiel and maybe they could have an even better night than the one before. 

“They look so good, don’t they?” A voice over at the other table said, loud enough that Dean knew it was meant for him. He looked over and saw Michael talking with Becky. 

“They do.” Becky was slightly drunk. Gabriel and Chuck had gone to the bathroom. Dean wasn’t meaning to listen, but he couldn’t help it. 

“I don’t understand why they broke up.” 

“Oh, she’s so perfect for him. I know that he says he’s happy with that man, but I just…look at them dance.” Becky’s voice was dreamy, like she was watching a couple in a movie. Dean couldn’t help himself. He looked at the dancefloor and saw Hannah and Castiel spinning around. They were talking and smiling and laughing. They looked like they were still in love. They probably were. What the hell had Dean been thinking? He was so stupid. He’d been used to make Hannah jealous, and it had worked. Dean drained the rest of his whiskey and made a decision. He began to walk out, but ran into Gabriel. 

“Hey Dean, you okay, buddy?” 

“Yeah, just a headache hit me hard. Can you give Castiel a ride home?” Gabriel looked taken aback for a moment, but nodded. 

“Yeah, of course. We’ll see you later, huh?” Dean nodded. 

“Thanks Gabriel, I really had fun this weekend.” Dean smiled. He meant it. Gabriel smiled and nodded. They exchanged good-byes and Dean left the barn. He gave one last look, knowing he’d likely never see any of those people again.

**Notes for the Chapter:**

> Thank you guys so so much for your subscriptions, comments, and kudos. You're all amazing and I love you all!


	13. Chapter 13

Castiel was spinning around the dancefloor with Hannah and actually enjoying himself. He knew he shouldn't be, but it felt familiar. It was nice. Much like being home. It was nice to visit, but the reality was that this wasn't where he belonged anymore. Hannah seemed to be happy as well. She even laid her head on Castiel's chest. 

"I have missed you." She whispered. Castiel stiffened. Of all the things he had expected her to say, that was not one of them. 

"Let's not forget who left who." Castiel really didn't want to talk about that point in his life. He was over it. He wasn't sure he would ever get over it when it happened, but now he had and he was okay with it. Hannah picked her head up from his chest and met his eyes. 

"I made a mistake." Castiel stared at her, hard. She was trying to get sympathy from him, but it wasn't going to work. 

"Obviously. Hannah, you left our home in the middle of the afternoon without so much as a face to face conversation about what we should do. Did you not think that I should have been involved in the decision to end our engagement and call off the wedding?" Hannah looked down for a moment and then back up at Castiel. 

"I'm sorry, I just got scared. We were always in bad moods towards each other and I thought you wanted out."

"I wanted us to talk about our relationship. You thought the answer was running away, apparently." Castiel was in no mood for this. She had had five years to contact him and she was just now saying all of this?

"Castiel, I wanted to talk to you, but by the time I had come to my senses you had left, and nobody would tell me where you'd gone." Now Castiel knew that she was lying. His mother would have told her anything she wanted to know. 

"Are you sure you're not just jealous because I have a new person in my life?" Castiel had suddenly realized that they weren't dancing anymore. He no longer had his arms around her, but she still had her arms around his neck. It felt odd. Why had he thought this to be a good idea, again? Hannah rolled her eyes. 

"Are you two really a couple? Your mother seems to think that this is all a show so that you could win me back. I think that's incredibly sweet, and..."

"My mother knows nothing. Dean and I have been dating for three months. He..."

"You have not. Michael seems to agree with your mother, by the way. This all seems like some sort of ruse to make it seem like you're over me. If you're not, that's great. You can come home and we could all be happy again. Your mother and father would love for you to come home." Castiel reached back and unwound Hannah's hands. This had been the last straw. 

"Hannah, believe what my mother says if you want, but I am telling you right now that I am incredibly happy with my life in Chicago. I am incredibly happy with Dean, and my job, and my house. I know that may sound absurd for everybody, but if you all can't accept that then just stay out of my life. Simple as that." Hannah looked like she was about to say something, but Bess had appeared out of nowhere. 

"Castiel! Dance with me, please?" Castiel smiled at her. 

"It would be my pleasure." Castiel nodded to Hannah. "Hannah, it was nice to see you again." Hannah didn't respond, but Castiel didn't care. He offered Bess his arm, she took it, and the two went to a different part of the dancefloor. 

"You looked like you needed some rescuing." Bess whispered. Castiel nodded. 

"You have no idea. Five years later and now she wants to fix our relationship." Bess bit her bottom lip. 

"I know, she mentioned that after seeing you with Dean last night. I think she was...I don't know...guessing you'd still want her?" Bess' word choice was odd, Castiel thought.

"Guessing? Not hoping?" Bess gave a small, humorless chuckle.

"Honey, look around, most of the people that made it from high school are married with kids. You and Hannah were supposed to beat all of us down the aisle. Don't get me wrong, I'm glad you guys didn't, but..." Castiel cocked an eyebrow. 

"Why are you glad?" Bess gave Castiel a bright smile. 

"Well, because you and Dean just might be one of the happiest couples I've ever seen. If you and Hannah had gotten married, oh sure you would've been mostly happy, but there would've been something missing. I know that I haven't been around you and Dean a lot, but I was around you and Hannah all the time, and you two, you and Dean, just...work better." Castiel gave a lopsided grin, his best Dean impression. 

"Thanks, Bess. I think I needed to hear that." That was the truth. Castiel knew that he and Dean should at least give it a try. Maybe they could take it slower than they had. Not having to jump into a three-month relationship. But dates, and coffee, and falling asleep in front of the TV because they both had had long days, leading to cuddling in the bed because they both were too tired to take it any further. But then, oh then, there would be the nights like Castiel had dreamed about. Where their kisses weren't interrupted by dads or brothers, and they could enjoy each other. 

"You okay, Castiel?" Castiel realized that he hadn't been paying attention to what Bess had just said. 

"Yes, sorry, you were saying?" Bess beamed. 

"Just that I know this was hard for you and I am so happy that you made it home, for me." Castiel leaned in and gave Bess a kiss on the cheek as the song ended. 

"Me too." A man that Castiel did not know came to cut in and Castiel gave Bess a hug before walking back to his table. He noticed that the table was empty, so he glanced up at the bar. He saw Gabriel, but no Dean. Maybe he was in the bathroom? Castiel started walking to the bar, but was cut off by his mother. 

"Sweetie, will you dance with me? I've already danced with your father and brothers, it's your turn." Castiel smiled stiffly. He knew his mother had had a little too much champagne. 

"I would love to, but I need to find Dean first." 

"Oh, he just ran outside. I saw him go out there for some fresh air. Now come on, dance with your mother." Castiel sighed internally and then took his mother's hand. He stayed on the edge of the dancefloor so he could see if Dean came back inside. 

"You look so handsome. You and Hannah looked so good dancing together.” Castiel rolled his eyes.

"I wouldn't get used to it. It was for old time's sake, I believe is the wordage she used." Becky sighed. 

"Are you sure? You two seemed to be enjoying yourselves. You two just…"

"Mother,” Castiel raised his voice slightly. “I am tired of this conversation. I am with another person that makes me happy and I am not getting back together with Hannah, regardless of what everybody else wants.” Becky nodded, indicating that she wasn’t going to bring it up anymore. He really didn’t want to talk about Hannah, but he did want to know the answer. “Did Hannah ever come talk to you after I moved to Chicago?" Becky looked towards the ceiling, as if trying to recall. 

"No, I don't think so." She looked back to her son. "I ran into her at the supermarket on occasion, and we would exchange small talk, but I don't think she ever came back to the house. Why do you ask?" Castiel shrugged. 

"Just curious." Once the song was over, Becky patted Castiel's cheek and Castiel finished his walk to the bar, where Gabriel still was. He had glanced over to the table just to make sure that Dean still wasn't back inside. He wasn't. 

"Gabriel, have you seen Dean?" Castiel tapped Gabriel on the shoulder. Gabriel nodded and took a sip of his drink. 

"Yeah, he went home." Castiel's eyes widened, and Gabriel held up his hands as if Castiel was going to hit him. 

"Chill out, he said he had a headache and was going home. He's probably taking a little siesta and he'll be back." Castiel eyed his brother. 

"I'm going to call him." Castiel pulled out his phone, but Gabriel took it away. 

"Let the guy sleep. You had him up late last night." Gabriel gave a suggestive wink. 

"I...I have..."

"Yes, you do. You know the basement isn't sound proof and you two weren't exactly quiet. Pretty sure nobody else heard anything, but," Gabriel smirked. 

"Shut up, Gabriel. Let me have my phone." 

"Here, I'll send him a text, and if he responds, you can take my car and go home. If he doesn't, you have to stay here with me and drink." Gabriel had already unlocked the phone and was typing. 

"How did you know my passcode?" 

"Your birthday. Not very original, Cassie." Gabriel looked to the bartender. "Sir, two of whatever these were." Gabriel taped his glass. The bartender nodded and started mixing something in the shaker. 

"So, how'd the dance with Hannah go? It seemed like you were enjoying it." 

"I did for a moment or two, but I was going to ask Dean to dance afterwards, but that apparently isn't going to happen." Castiel took his glass from the bartender with a nod of thanks. 

"I told you he'd be back. What's the worst that could happen?" The brothers exchanged smiles and clinked their glasses together before taking a drink. 

Dean packed all of his clothes back into his duffel. He had changed into the jeans and t-shirt he was going to wear to the brunch, but there was no need now. 

He had never done this. He'd never left in the middle of job, but he didn't have a lot of other options. He supposed he could call Sam, but Sam would probably just tell him to do whatever made him happy. What would make him happy to is go back to that barn and kiss Castiel so hard he'd never even remember Hannah. That, however, was not realistic. He could do what he had control of, which was leaving. He probably would ruin the rest of Castiel's weekend and make him answer embarrassing questions, but Castiel would have Hannah, and that was what was important, Dean supposed. Castiel's happiness. That's what the weekend was about, wasn't it? People being happy, and in love, and...shit. Dean hadn't said goodbye to Garth. Oh well, he could always send a card. Dean hoped that Gabriel would be able to help Castiel see this was better. Dean was pretty sure that Gabriel was catching on, but even if he wasn't, he was good big brother. Dean knew because if something similar had happened to Sam, Dean knew he'd be right there just like Gabriel was going to be there for Castiel. Dean sighed and then looked around for a notebook of some kind. He found one in the desk and quickly wrote out a note before leaving the house, thankfully before anybody got back. He turned his phone off, and took off into the night. 

Cas,  
I'm sorry. I just couldn't sit there and watch you be happy with her. It hurt. I broke the number one rule of my business; I got feelings for you. I know that's not something you would expect to hear from a hired date. I've been around enough relationships to know when people are supposed to be together, and you and Hannah should be together. Thanks for a fun weekend though.   
I left you enough cash to catch a flight back to Chicago, if you decide to come back.   
Have a great life,  
Dean

Castiel crumpled the piece of paper in his hand. 

"His clothes from the bathroom floor are gone, too." Gabriel came barging in the room, and Castiel wiped the tears from his eyes. 

"I should've come home when you told me he had left." Castiel looked at his older brother. "I should have taken your keys and come home. I can't believe this happened to me again."

“I should have let you go. Castiel, I am so sorry.” Castiel shook his head. He and Gabriel had come home nearly two hours after Dean had left, and Castiel assumed he would find Dean. He had called and texted, but Dean’s phone appeared to be off. 

“I have to get home.” Castiel declared, standing up from the bed. Gabriel nodded. 

“I’ll drive you to the airport.” Castiel quickly got everything into his bag and the two quickly left the house. 

“Where should we go? St. Cloud or St. Paul?” Castiel looked when the next flight was at both. 

“There’s a flight to Chicago in three hours at St. Cloud. The traffic would be less there since it’s only domestic flights.” Gabriel nodded and pressed the gas pedal even harder on their way out of town. 

Castiel was spinning his phone in his hand, hoping that he would get a call, a text, anything that would be from Dean. 

“So, what did the note say?” Castiel had thrown that in his bag, wanting nobody to find it. Castiel sighed. 

“That he wasn’t happy seeing me with Hannah. He thought that we looked happy together. That he wanted me to be happy.” 

“Cas,” Gabriel sighed, and Castiel nearly made a noise of protest at the nickname, but decided not to. “Are you sure there’s nothing else going on? I feel like that’s a pretty piss poor excuse for just leaving you.” Castiel debated telling Gabriel the truth. 

“I…we’ve been up and down lately. We had a bad fight before we got up here.” Castiel lied. “About Hannah and seeing her again. I knew it was stupid to dance with her, but I did it anyway. It was stupid.” Gabriel exhaled and nodded. 

“Okay,” was all Gabriel said before remaining silent for the rest of the trip. 

They pulled into the parking lot of the airport so that Castiel could leave. 

“Call me when you get there and let me know how it goes.” Castiel nodded and got out of his brother’s car. He leaned his head in the car. 

“I will, and tell everybody that I’m sorry we had to leave.” Gabriel nodded this time. 

“Bye, bro.” Gabriel drove away and Castiel walked inside to buy his ticket home.

**Notes for the Chapter:**

> Thank you guys SO much for your kudos, subscriptions, and comments. They mean so much to me. I am so glad you all are enjoying this story.


	14. Chapter 14

Dean felt like a kid being called into the principal’s office. He was standing in front of Crowley’s door, waiting to be called in. He had to quit. He couldn’t risk getting involved just to be another pawn.

“Dean, I know you’re out there,” came the gruff voice through the door. “Come in.” Dean walked in and saw him sitting at his desk. He wasn’t a tall guy, but he held a lot of power, and that made him intimidating. He gave Dean a quick glance and nod before going back to what Dean assumed was a contract on his desk. “Take a seat, Dean.” Crowley signed the paper and then looked at Dean expectantly. After a few seconds of silence, Dean broke it. 

“You called me in here.”

“There are rumors about you around this place, Dean. That you…left early.” Dean had called Meg on his way home so that she could let Crowley know that he’d broken his number one rule. Well, technically two, but he’d already broken number one, so may as well break number two. He’d seen the calls and texts from Castiel, and made a mental note to change his phone number the next day. “Is that true?” 

“Yeah. I did. And I want to quit.” 

“You can’t.” Crowley stood up and walked to his file cabinet. He pulled out a similar looking sheet of paper to the one that was on his desk. “You’ve signed a contract.” 

“Which expires in a month.” Dean threw back, giving Crowley a smirk. Crowley’s eyebrows furrowed and he looked at the paper. His face went from confused to understanding to furious. He looked over to Dean. 

“So, what? This is the one that just swept you off your feet? Fallen in love after a weekend? Can’t wait for the movie.” Dean clenched his jaw, but didn’t say anything. 

“Look, I’m leveling with you, man to…whatever you are, that I’m not renewing my contract. My Uncle Bobby is going to give me a job I’ve been in this business for too long.” Crowley rolled his eyes and moved back to behind his desk. 

“Dean, you’re one of my best, I’d really hate to lose you. What if we up your pay? I do love negotiations.” Dean shook his head. 

“Nah, I’d rather just not renew my contract. You don’t need me.” 

“Of course, I don’t need you, that doesn’t mean that I want to lose you.” 

“Thanks, Crowley, that really helps. Now, can I go home? I’m tired.” Crowley waved him off. 

“Fine, fine. You’ll be back though.” Crowley sat down and began reading something else. Dean stood up and offered his hand, but Crowley didn’t look up, and Dean started to walk away. Crowley didn’t say anything else, but Dean knew it was going to be bad for business. He didn’t really care, he just knew that he needed out of there. 

“So, you’re leaving, huh?” Meg called from her desk as Dean walked past. 

“Yeah, in a month. My contract is up and I just need to get out of here. It’s not…”

“The guy was it, huh? You’ve never left early and now you’re quitting. I just…I didn’t know this would happen.” Dean raised an eyebrow. 

“What do you mean?” 

“I just thought it was going to be a fun weekend when I got the call. You were the only one available and…” Dean put his hand Meg’s shoulder. 

“Meg, stop. I’ve been thinking about leaving for a while now. I’m glad you booked that for me. It made it my time. I’ll come back to visit.” Meg gave him a small smile. 

“No, you won’t. But, we could go out some time.” Dean nodded. 

“Sounds good, now I really have to go. I’m meeting Benny at a bar.” 

“The Roadhouse?” 

“Nah, some place new.” Dean and Meg exchanged goodbyes and Dean left, knowing he didn’t have to work for the next three days. And he needed that. 

Castiel landed at O’Hare Airport, and quickly grabbed his bag from the overhead bin. He wasn’t sure how he’d get home to his car, but he would find a way. He needed to find Dean. He calculated between the time that Dean should have gotten home and how long it would take him to get back. They should have been about equal, factoring in that Dean would need to stop for gas. 

Castiel hailed a cab much quicker than he thought he would (and may have stolen it from a couple that seemed to speaking rapid German to each other), and barked his address to the driver. The driver simply nodded.   
“Ya just gettin home, pal?” The driver asked, eyeing Castiel in the review mirror. He had a thick Chicago accent which, even after living in the city for five years, still threw Castiel. 

“Yes.” Castiel replied, annoyed that the man was trying to make small talk. He just needed the get home. Perhaps the driver picked up on that attitude because he didn’t say much else except for Castiel’s total once they arrived. Castiel gave him a nice tip for that. He quickly ran inside, deposited his bag on his couch, and then looked around for his car keys. He had detached them from his house key for the weekend, but now he couldn’t find them. As he searched, Castiel asked his phone for directions to Crowley’s. 

“Crowley’s Lounge is fif-teen minutes from your location. Here are your directions,” the cool female voice countered Castiel’s mood. He didn’t even know if they would give him the information but…”Better hurry. This location closes in less than thirty minutes.” Shit. Castiel finally saw his keys under his dining room table and quickly grabbed them. He ran out to his car and took off. 

“Is Dean here?” Castiel demanded from the girl at the front desk. She had a round face and dyed blonde hair. She had large brown eyes and gave Castiel a smile. Her voice was soft and deep. 

“No, he’s not, but is there something I can help you with?” She looked Castiel up and down. 

“Could you possibly give me his address? I really need to speak with him.” Her mouth formed in a hard line. 

“I’m sorry sir, we don’t release that information.”

“You don’t understand,” Castiel knew that he was probably going to get that for an answer. 

“I think I do. Look, we cannot release that information.” Castiel felt his face fall. He knew that this was a long shot, but he had been hoping Dean would be there. Castiel sighed, thanked the girl, and turned to leave. “But if I were looking for Dean, I’d check The Roadhouse or Singer’s Auto just outside of town.” Castiel turned around. The girl gave him a closed lip, genuine smile, and then shrugged. “But hey, that’s just if I was looking for him.” Castiel grinned back to her. 

“Well, I appreciate your time.” She nodded at him and Castiel left as quickly as he could. He asked his phone again for directions to The Roadhouse. 

“There are three places called The Roadhouse in your area, all of which close soon.” She replied. “To which are you referring?” Castiel sighed. 

“Close out.”

“Okay.” The phone beeped. Castiel wanted to try one more thing. 

“Directions to Singer’s Auto.”

“Here are your directions. This place will be closed when you arrive.” Fuck. 

In the morning, Castiel got out of bed. He didn’t sleep very much, but he figured if he got to Singer’s early enough, he could talk to somebody about Dean and then maybe he could find him. He found out where to go and decided to try to get there before they got busy. 

Castiel wasn’t sure he was in the right area when he pulled in. This place looked more like it belonged in the middle of nowhere, not just outside the busy city of Chicago. It nearly looked like a barn, but it seemed to be relatively clean. He also saw a sign that said “Singer’s Auto” just above the door. There was an “OPEN” sign flashing just beneath that. Castiel parked his car and walked in. The bell above the door jiggled and Castiel heard a voice from the back. 

“Give me a minute!” A gruff voice shouted. Castiel saw pictures along the back wall and Castiel knew he was in the right place. There were a few of Dean intermixed with other people. Dean with a woman with long brown hair and another woman with long blonde hair. A younger Dean with a boy with shaggy brown hair. Dean with two men, both with beards, one younger and one older, standing in front of the shop. 

“Sorry ‘bout that, can I help ya?” The younger man from the picture came out, tucking a rag into the back pocket of his overalls. He seemed even bigger out of the picture. He looked solid with beefy arms. 

“I um…hi, I’m Castiel.” Suddenly, the man’s blue eyes went hard. 

“Oh.” Castiel didn’t like the way this was going to go. “Is there somethin’ wrong with your car or…?” 

“Actually, I…I heard from somebody Dean might…”

“Well, you heard wrong. So, if there’s nothin wrong with your car, you have a good day now.” Normally, Castiel would have admitted defeat, but he wanted to know something. 

“Are you his boyfriend?” The guy folded his arms, making him even more intimidating, practically doubling his biceps. 

“Maybe I am. Even if I’m not, Dean doesn’t need anythin from you. Now, like I said, you have a good day.” Castiel was going to push him, but after noticing the look in the man’s eyes, Castiel decided to wait until The Roadhouse opened and see if Dean showed up. He had discovered which one he would need to go to, and if he had to wait all night, he would wait all night. 

Castiel left the shop and got into his car. He pulled out of the parking lot and started driving back to his home, trying to figure what he would even say to Dean. The Roadhouse didn’t open until six o’clock that night. What was he going to do for the next seven hours? Castiel decided to go home, try to read, possibly go on a run (even though he hadn’t done that since he first moved to Chicago). He needed to get out of his own head, so Castiel drove home, changed, put his headphones in his ears, and took off, hoping an idea would hit him while he was running. 

“Come on, brother. I want to see Jo.” Benny took a sip of his beer in the garage. They normally didn’t do this, but Bobby and Ellen were out of town until tomorrow morning, so they were drinking a beer before they headed to a bar. 

“You always want to see Jo, why don’t you two move in together already?” Dean asked, mostly joking. Benny and Jo had met at Northwestern, but had only been friends until last year. They were one of the best couples that Dean knew. They fought, a lot, but it was mostly fake fights or teasing each other. Dean secretly wanted a relationship like that. He had been hoping… No. He wasn’t thinking about that tonight. Or any other night. Tonight, he and Benny were going to go out, get drunk, and not move much if at all the next day. 

“You know Ellen would never let us move in together until we’re engaged.” Dean laughed. 

“Yeah, you’re right. Alright, fine. We can go see your girlfriend.” Dean gave Benny’s shoulder a push before draining his beer and stood up. “Let’s get going.” Benny copied Dean and two got into Dean’s car and drove to The Roadhouse. 

Castiel waited for the blonde woman (that he was pretty sure was the same from the pictures at the garage) in the window to switch the open sign on. He thought he was going to be alone in waiting, but there were a few other cars waiting (and with a slightly crestfallen look around, Castiel realized that Dean’s wasn’t among them). The orange light flicked on and Castiel walked inside. The first one in. The girl moved behind the bar and smiled at the people that walked in behind him. 

“Hi, there! Come on up!” Two men sat in booths and a third walked and sat at the bar. Castiel followed him and sat a couple seats away. He turned to watch the door, his back to the bar. 

“Hey, handsome.” Castiel jumped and turned around. He was face to face with the woman. She smiled. “I don’t think I’ve ever seen you in here. I know this isn’t exactly a small town, but…”

“I heard about this place from a friend. Actually,” Castiel was hoping that she wouldn’t have the same reaction the man at the auto garage had. “You may know him. His name is Dean Winchester.” The young woman smiled.

“Oh sure,” her smile faltered for a moment. “How do you know him? From work?” Castiel wasn’t sure if the girl knew what Dean did for a living, so he didn’t know if he should lie or not. He decided he could cover it up another way if she knew. 

“Yes.” The girl frowned. 

“How do you know him from work? Did you and he…?” 

“JO!” Castiel turned around at the name, and saw the man from the garage and…

“Dean.” Castiel breathed out. He thought that he had figured out what he was going to say, but he apparently was wrong. Castiel turned back around, hoping they hadn’t noticed him. The girl that must’ve been ‘Jo’, wasn’t there. She was walking behind the bar and then disappeared out of Castiel’s eyesight. He didn’t hear them say anymore, but he was sure they were whispering to each other about him. Castiel sat, hoping Dean would be the one to walk up to him. He was wrong. 

“Thought I told you to leave Dean alone.” Castiel looked to his left. The man was there again. 

“I just need to talk to him.” Castiel turned and saw Dean watching with Jo. “Dean, please?” 

“Look, man…” 

“Benny,” Dean finally spoke. The large man looked over to Dean. “I’ll take care of him. Castiel, can we do this outside?” Castiel’s heart sped up. He stood up and walked over to Dean. Dean nodded at Benny and squeezed Jo’s shoulder before walking out the door, and Castiel followed. Dean leaned against the front of the bar and crossed his arms. 

“What do you want?” There was that attitude that Castiel thought he had gotten rid of earlier in the weekend. 

“Well, I was actually hoping you would apologize to me.” Dean’s eyes widened. 

“ME apologize? You’re kidding me, right? You were dancing making goo goo eyes at your girlfriend and…”

“You LEFT me!” Castiel was suddenly angry. “I wasn’t making goo goo eyes at anybody but YOU all fucking weekend and you left me!” Dean’s eyes narrowed. 

“Really? That’s why your brother and mom were talking about you two getting back together and living the life you were supposed to?” Dean was exaggerating, but he didn’t really care. He wanted to push Castiel away. He didn’t want to deal with the feelings he had. He didn’t want to pretend that Castiel was actually there for him. Castiel was quiet for a moment. 

“You really think that I want to be with her?” Castiel’s voice was quiet. So quiet, Dean wasn’t sure he had heard correctly. Castiel looked into Dean’s eyes. “If I wanted to be with her, why would I be here? Why would I have left her, and one of my best friend’s wedding, and come here?” Dean stared at him for a moment. 

“Because it would blow our cover. You would have to admit that everything was a fucking lie and tell your family that the only reason you had me there was to make it seem like you were over Hannah, which obviously, you’re not. Can I go back inside now?” Dean pushed himself off the wall but Castiel pushed him back against it and pinned him there. Dean widened his eyes as Castiel got so close their lips were almost touching. Dean could feel Castiel’s breath. 

“No. You can’t just fucking leave me like this. Not when you say things like you got feelings for me. That you broke a rule because of me. Not when I’ve been thinking of ways to get you back since I found that you were gone and I read that stupid note. You don’t know how much it hurt reading that. I don’t want Hannah, I want you.” Dean was about to reply when his lips were suddenly occupied with something else. He kissed Castiel back. 

Castiel wasn’t sure if Dean was giving him pity or not, but he didn’t care. He was going to take advantage of it. Dean pushed against Castiel slightly, but Castiel pinned him back against the wall. Dean slid his fingers into Castiel’s belt loops and pulled him even closer. Castiel took it as a good sign, until Dean pulled away. 

“Cas,” He whispered, shaking his head. Castiel thought that he could feel his heart breaking in a million pieces. “We can’t do this here. Benny and Jo will give me all sorts of hell. Let me say bye to them and we’ll go.” Castiel’s head was still spinning, but he nodded and moved away so Dean could run inside. Dean handed Castiel his keys, and then pulled him in for a hard, quick kiss. “Go wait in my car.” Dean growled before running back inside. 

Benny was at the bar, talking with Jo and drinking a beer. He saw Dean approach and smiled widely.   
“You’re leavin.” It wasn’t a question. 

“Yeah. I’ll see you at the garage tomorrow.” Benny snorted. 

“Like hell you will. Now get out of here.” Dean smiled and ran back out to his car where Castiel was waiting.

**Notes for the Chapter:**

> UGH! You guys, I'm so sorry this is late. Family stuff got a little out of hand the last couple of weeks, so I'm so sorry. I love you guys, and thank you so much for your subscriptions, kudos, and comments. They mean the world to me.


	15. Chapter 15

Dean drove as fast as he could back to his place. He didn't care that he hadn't cleaned it since he got home and all of his clothes were strewn about since he'd gotten home. He had his hand on Castiel's thigh, slowly moving it up and down on the way home. He thanked God for the umpteenth time that he didn't live far from The Roadhouse. 

"Dean," Castiel moaned as Dean moved his hand into Castiel's crotch. 

"Sh," Dean insisted as they pulled in to his driveway. Dean had never done this. Wow, he felt like he'd been saying that a lot with Castiel around. He never got feelings for a client. He never left a job early. And he never, under any circumstances, allowed a client into his house. Hell, he didn't even like it when the clients were in his car. But this, Castiel. He was different, and Dean had known that since they first met. 

"Let's get inside." Castiel nodded as Dean the led the way to his house. Once inside, the two wasted no more time. Dean had Castiel pinned against his door by his hips. Castiel whimpered when Dean kissed around his next and face, but not his lips. 

"Dean," Castiel groaned again. Dean smiled and met Castiel's eyes. 

"You ra...?" Dean's mouth was suddenly occupied by Castiel's. Their lips met in a clash of tongues and teeth as they began to strip off their clothes. Dean grabbed Castiel's hand and dragged him into his bedroom. Dean slid Castiel's pants off and pushed him on the bed. He straddled Castiel's hips and Castiel pulled him down to meet his lips again. Dean could feel Castiel through his jeans. 

"You're going to remember this time. I gaurentee it." Dean growled before slipping Castiel's shirt off. Castiel looked up at Dean. 

"Wh...what do you mean?" 

"You didn't remember last time, but I'll make sure you do this time." Dean's mind wasn't really paying attention to his mouth, but he felt Castiel's hands on his chest and looked at him. "What?" 

"We've had sex?" Dean saw the look in Castiel's eyes change from lust to confusion. Dean nodded. 

"I...when?"

"The night before last. You were drunk, and we...well, we we went down to that other bedroom and..." 

"I should have remembered something like that." Castiel replied before pulling Dean back into a kiss. Dean didn't argue and kissed Castiel back. Casitel and Dean continued stripping off the other's clothes until they were down to their boxers. Castiel now understood why the 'dream' he'd had felt so real. It had been real. He knew that now. And they could talk about Dean lying to him later, but right now, he wanted this moment with Dean. 

Dean kissed down Castiel's neck and chest. Castiel wrapped his fingers in Dean's hair as Dean gently traced the waistband of his boxers with his lips and tongue. 

"It's not nice to torture people." Castiel whispered heatedly. Dean chuckled and Castiel felt the breath through the fabric of his boxers on his overly sensitive cock. 

"You're right, it's not." Dean gave Castiel a smirk, reminding Castiel of not even five days ago. The man that walked into his house with coffee and was now Castiel was in bed with him. Dean slid Castiel's boxers off, freeing his hard, leaking cock. Castiel sucked in as the cool air in the room hit it. Dean gave Castiel a wink before slowly taking Castiel in his mouth. Castiel groaned. Dean's mouth was wet, and hot, and his tongue was skilled. It moved up and down Castiel's member and traced the vein on the underside before swirling around the head. Castiel was moaning and pulling on Dean's hair as he got a blow job like none he'd ever had. He could see Dean reach down and work himself with his hand. It was a strange, even more arousing, sensation to watch him. Castiel could feel that he was getting close. 

"De...Dean?" Castiel panted, hoping to give Dean a proper warning, but Dean didn't pull off. He hollowed out his cheeks and Castiel wasn't sure he could even make coherent sentences anymore. He tried to pull Dean away, but Dean held onto one of Castiel's thigh, keeping him inside until Castiel came with a cry and Dean swallowed him down. He pulled off Castiel and then finished himself, coming onto the bedspread. He made his way back up to Castiel's face and smiled at him. 

"You going to remember that?" Castiel laughed, mostly with humor. 

"For a long long time." Castiel smiled over at Dean. Dean laid back and Castiel rested his head on Dean's chest.

"Good, that was my intention." Dean wrapped his arms around Castiel and placed a kiss on his forehead. The two were quiet for a few long, blissful minutes, before Castiel remembered they should probably have a conversation. 

"Dean," Castiel even heard his voice was deeper than normal, something that he wasn't sure was possible. 

"Hm?" Dean opened his eyes and looked at Castiel. 

"We um...we should probably talk about the weekend, right?" Dean sighed and nodded. 

"Yeah, we probably should. But, can it wait until morning? I think in couple minutes we'll need to make up again." Dean smiled and Castiel returned it.   
The sun was coming through the window and Castiel rolled over so that he wasn't blinded. He cracked one of his eyes open and saw Dean’s chest raising up and down. Castiel smiled to himself and wiggled closer to Dean. Dean’s arms tightened around him and Castiel tried to think of a time where he had been this happy. Dean sighed sleepily and then opened his eyes. Castiel opened his other eye and smiled. Dean grinned back. 

“Good morning, sunshine.” 

“Hello, Dean.” 

“Want some breakfast?” Castiel nodded and Dean pressed a kiss to Castiel’s head before they both sat up and Dean pulled his boxers on before walking out of the room. Castiel stood up, but his knees shook slightly. He had never had a night like that. Dean had…well, Castiel definitely was not going forget it, like Dean had promised. Castiel was about to get into his boxers before he heard his phone ringing across the room. He sighed, pulled his boxers on, and walked over to his jeans and pulled it out of his pocket. Gabriel was calling him. Castiel slid the screen to answer. 

“Hello, Gabriel.

“Hellooooo, Cassie. I’m assuming you found your boyfriend?” 

“I did. We made up. Is something wrong?” 

“Well, I was trying to figure out more about Dean, so that I could try to help you a little bit more. You’ll never guess what I found.” 

“Um…no idea.” Castiel replied, but he could barely hear from the ringing in his ears. 

“You said that Dean works at a car shop, right?” 

“He’s a mechanic, yes.” 

“And you two are REALLY dating, huh?” 

“Yes?” Castiel sat back down on the bed, not sure he could stand anymore. He knew what was coming. 

“You didn’t…pay him to come up here?” Castiel sighed and rubbed the bridge of his nose. 

“Look, Gabriel,”

“All I need is you to be honest with me. Did you, or did you not, pay him to come up here with you?” 

“Are you alone?” 

“Yes, I’m on my way to the airport right now, so you better tell me what the hell is going on.” Castiel decided to be honest. 

“Yes, I paid him.” Gabriel made a sound of shock, but not of disgust, which Castiel had thought he would hear. 

“Then, why was is such a big deal that he left?” Gabriel asked gently. 

“I…I originally was going to just bring him as my date and say we broke up not long after we got back here, but, I…I…he and I…we…” Castiel was having trouble articulating what he and Dean were now, or what point exactly Dean had turned from a hired date into the real thing. Maybe it was when he realized that Dean was comforting him with the hand squeezes, or when Dean and he had kissed on that first night, but whenever it happened, it happened. 

“You love him?” Castiel absorbed his brother’s words for a long moment. He was about to reply when Gabriel spoke again. “You don’t have to answer, but, you know what he does, so how is that going to work?” Castiel thought for another minute. 

“We haven’t talked about things yet, but we will.”

“What were you doing last night, then?” Gabriel’s voice changed from one of scolding to one of implications. 

“None of your business, but thanks for the concern. Have a nice flight back to California.”

“Aw come on, Cassie! I’m proud of you getting it for real and not paying it!”

“Hanging up now.” Castiel quickly pressed the button that hung up the phone. He looked around Dean’s bedroom and sighed. Well, at least he had come clean to somebody. And Gabriel had brought up a good point about Dean’s job, but when was Castiel supposed to ask Dean about it? Just during breakfast, or should he just let it slide until Dean brings it up? Maybe…

“Cas?” Dean appeared in the doorway wearing an apron. “Ya coming?” He grinned that stupid grin that made Castiel’s heart melt. 

“Yeah, I just um…got a call from Gabriel.” Castiel’s tone must’ve held something he hadn’t intended because Dean’s smile faded. 

“Oh. And um…what did he say?” Dean walked in and sat next to Castiel on the bed. 

“That he found out who you were. What your job was…is.” 

“Is he going to tell your family?” Dean’s lips formed in a hard line. 

“No, Gabriel wouldn’t say anything.” 

“But if found me that means somebody else could and…” It was finally Castiel’s turn to place a comforting hand on Dean’s knee. 

“If that happens, we can always pretend that you have some evil twin hell bent on taking your life over.” Dean chuckled, took Castiel’s hand and intertwined their fingers. 

“Well, the good news is, in a month, I’ll be off the website and Crowley scrubs stuff clean so that people can’t be found again.” Castiel glanced at Dean and tilted his head.   
“What do you mean?” 

“I mean that we sign a contract, and once it’s up we can either resign or let them go and quit. I’m not resigning mine. I’m going to go work for my uncle at the garage.” Castiel was quiet for a moment, playing with his and Dean’s hands. 

“Because of me?” He whispered. He couldn’t even fathom that Dean wanted to give up everything for him. Hannah hadn’t even wanted to work out their relationship, but Dean was willing to change his career for him. 

“Yeah, because of you. Because I finally found somebody that…I…I don’t know. It just seemed like the right time.” Dean cleared his throat like the last sentences had scratched him. 

“I would appreciate you having a different job.” Dean smiled over at Castiel. Since they were having, one of the closest things they had to a heart-to-heart, Castiel decided to try and ask something that had been bothering him. “Why did you leave?” Dean looked down at the floor, his hand tightened around Castiel’s. 

“I saw you with her.” Dean’s voice was quiet as though he didn’t want Castiel to hear. “I just thought…your family and you would’ve been happier with her. I figured if I just bowed out, no harm no foul, ya know? And I could just hear the way they were talking about the two of you and watching you with her was like…damn it, Cas. It hurt. It hurt everywhere. That sounds stupid, but I was used to being...well, used. And I thought that was all I was being again. I had imagined everything. The feelings when we kissed, when we touched,” Dean let go of Castiel’s hand and traced one of his wings. “When you told me about your wings and what they meant to you. I just wanted you to be happy, and I didn’t think I could do that for you.” Dean’s eyes were still on Castiel’s tattoos and tracing them. Dean leaned forward and placed a kiss to one of his feathers. 

“Why?” 

“Because, I…I don’t do that. I make people happy for a weekend and then I leave. I’m just an escort.” Dean continued tracing Castiel’s wings with his lips. 

“That’s not true.” Castiel moved so that he could bring Dean’s lips to his own. “You, Dean Winchester,” Castiel trailed kisses along Dean’s neck and shoulder. “Are so much more than that.” Castiel took Dean’s lips again. Dean kissed him back before pulling away. 

“Your breakfast is getting cold, and some of us have work we need to get to.” Castiel stiffened. 

“You have to work?” 

“I have to go talk to Crowley about my weekend. Give him…ya know, a cut.” Dean stood up and pulled Castiel with him. “Come on, I don’t want to talk about work.” Castiel nodded and followed Dean out to for breakfast. And if Dean was just a little late (okay, a lot late) to his meeting with Crowley, so be it.

**Notes for the Chapter:**

> Again, so sorry this is late. This is just about wrapped up though! Thank you guys so much for your comments, subscriptions, and kudos. They mean to the world to me and I love you ALL!


	16. Chapter 16

Dean parked his car in employee lot and walked into Crowley's. Meg was on the phone and looked up at him. She held up a finger to Dean and Dean stopped at her desk. 

"Yes, sir." Meg rolled her eyes at Dean and smiled. "Yes, sir, she'll be there. Yes, she's a natural blonde. Thank you for choosing Crowley's." Meg hung up the phone and looked at him. "Some people are so picky. So, Crowley isn't here." Dean cocked an eye brow at her. 

"He's not?" 

"No, so he just wants you to drop the money off with me and I'll get it to him." Dean clicked his tongue. 

"He's pissed about me leaving, isn't he?" 

"Well, yeah, that too. But he really isn't here. And since he isn't, do you want to tell me about your weekend? What REALLY happened?" Dean took the envelope out of his back pocket and handed it to her. 

"I don't know, Meg. He was a good kisser. And..."

"Apparently great."

"We just hit it off. You know I don't do emotions well." Meg nodded. 

"I know, but come on he…” Meg stopped her sentence short and cast a glance over Dean’s shoulder.

"Dean." Dean sighed and turned around. He’d know that voice anywhere. 

"Hello, Crowley."

"Here to beg for your job back? The answer is no. I've already got somebody to replace you. Somebody younger even. He'll be better." 

"I'm sure he will. No, I was just dropping off my pay from last weekend and Meg and I were talking." Crowley gave Dean a hard look. Dean smiled back. "She's got my money. Now if you need anything..."

"Did you get your new schedule for the week?" Meg handed him the piece of paper. Dean took it and held it up to Crowley.

"I do now. Can I go? I've got...company." Crowley raised an eyebrow.

"Company? Not that...Castle person?" 

"Castiel. And it's none of your business. You got his money,"

"If you didn't take a cut, I think I should get all of his money, don't you?" Crowley sneered. 

"Now that would be a breach of contract, and I know you're a stickler for that." Dean winked, thanked Meg, and headed out the door before Crowley could do or say anything else. He was hoping that Castiel was still okay at his house. He invited him to take a shower, sleep, eat, do whatever, but he also figured that Castiel hadn’t moved much. He had fallen back asleep just before Dean left for Crowley’s. Dean was going to go home spend as much time with Castiel as possible before going back to work. This was just a simple dinner with the family from out of town. They had already discussed nothing more would come of it. Just enough to get the parents off the woman’s back. 

Castiel rolled over to glance at the clock. It was just shy of ten in the morning. Dean said he would be back within the hour, but Castiel wasn’t sure why he’d woken up. Until finally, he found the source of the obnoxious ringing was coming from his phone. He answered it without looking. 

“’lo?” 

“You fucker.” Castiel sighed. He’d recognize that voice anywhere, anytime. 

“Charlie, it’s a little early for obscenities, isn’t it?” 

“Not when I haven’t I talked to you in like a week and I have no FUCKING idea what happened to you after Saturday!” 

“Look, him and I…”

“No, no, no, we need to talk face to face.” Castiel sighed. 

“I’m not…available to talk right now.” 

“Where are you?” 

“I’m…um…I’m in his house. He’s…”

“WAIT WHAT?! You…I…fine! Fine, but tomorrow, during your lunch break we’re going to out and you are telling me EVERYTHING.” 

“Don’t you take lunch at like two thirty?” 

“Oh please, the new boss loves me and doesn’t know I’m in a committed relationship with the love of my life.”

“That happens to be a woman.”

“No, she knows that.” Castiel laughed. 

“Okay then, I’ll see you at lunch around twelve fifteen at that café a couple blocks away.” 

“Great. Just know that I am extremely upset with you and I cannot wait to yell at you in person.”

“Thanks, Charlie. See you soon.” Charlie mumbled a goodbye and Castiel hung up. He closed his eyes again, but heard the door open and sat up. He heard Dean pad up the stairs and open the door. Dean walked in and laid in bed with Castiel. He pressed his forehead to Castiel’s and smiled. 

“Honey,” Dean whispered. “I’m home.” Castiel smiled. 

“I can see that, thank you, Dean.” 

“Do anything fun while I was gone?” 

“Laid here. Talked to Charlie. How was work?” Dean shrugged. 

“I have another um…job tonight.” Castiel nodded. He felt a heat rise in his chest. He knew he only had to deal with this for the next month or so, but that didn’t mean he wasn’t jealous. 

“Who with?”

“Woman named Lisa. Just a simple date with the folks.” 

“You don’t need to meet her beforehand?” Dean shook his head. 

“I’m yours until about six fifteen. Then my name is Michael and I’m a dentist.” Castiel quirked an eyebrow. 

“People give you different names?” The profession thing didn’t throw Castiel as much as the name thing. 

“Oh yeah, all the time. I’ve been given all kinds of names.” 

“I like Dean.” Dean smiled, and Castiel smiled back. 

“Do you have to go to work tomorrow?” Castiel nodded. “Well, afterwards, would you want to get dinner? A proper date where we’re not spilling coffee on each other, or drunk, or pretending anything?” Castiel’s grin grew. 

“I would like that very much, Dean.” Dean pulled Castiel into a kiss. 

Castiel sipped his coffee and watched the doors to the café the next afternoon. He was tired, and needed an extra dose of caffeine. He and Dean had spent the rest of the day in bed until Dean had to go. Castiel decided to go home and finally get some rest. He took a shower and fell into bed, barely pulling the covers over himself before falling asleep. His alarm rang still too early and he got up for work. He got dressed and got to work on time. He was asked by a few people how his weekend was, and the wedding. He told them it was fine, good to see family again, and people were accepting of the story. He smiled at Anna and explained to her about his weekend. She seemed happy that enjoyed it.   
Now, he was just waiting…

“Castiel! I hate you so much right now that I just want to hit you!” Charlie smacked his arm and sat across from him. 

“Ow!” He rubbed his arm. “That was unnecessary.” Charlie glared at him. 

“No, unnecessary is you hanging up on me and then NEVER calling me back! I want to know how everything went and how he is and what happened so that you ended up at HIS HOUSE!” 

“Sh!” Castiel glanced around to see if anybody had heard her. She rolled her eyes as the waiter arrived. She ordered a tea and waited for the waiter to leave before she asked again.   
“You need to tell me about your weekend.” Castiel sighed and dove into his story. He paused when the waiter came back with Charlie’s tea and then continued. He knew that Charlie was eating the story up, and he didn’t exaggerate anything. He enjoyed the way she gasped, and widened her eyes, but didn’t interrupt him. He finished, nearly twenty minutes later, to a surprised Charlie. She sat quiet for a moment, and took a sip of her tea. 

“You love him.” Castiel opened his mouth, but Charlie held up her hand for him not to interrupt. “I know you won’t say it to him, and probably won’t for a long time, but I can see it. Castiel, you’ve never talked about anybody like this. I’ve heard you talk about Hannah, but even that doesn’t come close to this. You seem happy. You…oh, honey. I think you’re in love.” Castiel looked down at the table and smiled. Hearing it from Gabriel was one thing, but to hear it from his best friend, one of the very few people that he had opened up to since moving to Chicago, was different. It really made him think. Of course, she was right, Castiel wasn’t going to say anything, but there was a good chance that, if things went well tonight, he would be with Dean for a long time. 

“I am happy, in love? I’m not sure, but I am happy.” Castiel finished his coffee and placed money on the table for his coffee, Charlie’s tea, and a tip. “However, I need to get back to work.” Charlie nodded and drained her tea. 

“Me too, I was showing the pictures from ComicCon at work, and people said that Dorothy and I looked super cute so the new boss knows and won’t let me slack off anymore.” Castiel laughed. 

“We need to get together for that too!”

“What about tonight?” Castiel smiled and shook his head. 

“I have a date tonight.” Charlie squealed and clapped her hands. 

“Oh, that’s WONDERFUL! Have fun! We’ll figure something else out.” Charlie gave Castiel a kiss on the cheek before waving at him. “See you later!” Castiel smiled and waved to her. He followed her out and started walking the opposite direction of her to get back to work. 

Back at work, Castiel saw that he had a new email. From Bess. Shit. How could Castiel had forgotten to call her?

“Castiel,  
I hope everything is okay! Gabriel said that something happened to Dean’s uncle, so you guys had to leave. I’m so sorry, but let me know! I loved that you could make it home for our big day and that you and Dean were here. I really hope that everything is okay and I would love to see you guys again soon! Email or call or text or whatever!   
Love,   
Bess Fitzgerald”

Castiel figured that he could call her back on his way home from work. He did, and explained everything (well, made up something about Bobby getting into an accident). Bess was very understanding and told Castiel to give Dean her condolences. She offered Castiel another weekend up to Wisconsin, and Castiel told her they would think about it. 

Dean pulled at his tie, trying to make it comfortable. He wore ties all the time for work, so when he was at home, he tried to never wear them. This was different, though. This was a date with Castiel. Dean was planning the date, which was something that he hadn’t done for a long time. Castiel had asked what to wear, and Dean had told him to dress up. They were going to a restaurant that Dean knew the chef at, and had been promised a reservation. It was a newer restaurant, so they were often busy, but sometimes, dating around town all the time had its advantages. Dean checked his clock on the wall, and decided he should go if they were going to be on time. Dean grabbed his car keys and walked out. 

He picked up Castiel just before six, and their reservations were at six fifteen. Castiel was wearing something similar to what he had worn to the wedding, and Dean didn’t want to take his eyes off of him. 

“Wow, you look great, Cas.” Dean smiled as Castiel opened the door. Castiel beamed back. 

“Thank you, Dean. You look very well yourself.” They had begun walking to Dean’s car. Dean opened the passenger side door and Castiel slid inside. Dean walked around the other side and got inside. 

“So, how was work today?” Castiel shrugged. 

“It was fine, told everybody about the wedding, they seemed happy I had a good time.” 

“Good, and did you tell them about, ya know, us?” Dean glanced over before back to the road. Castiel was quiet. He hadn’t told anybody. “I’m not going to be mad, I just wanted to know.” 

“No, I didn’t. I didn’t know how to explain it.” Dean shook his head. 

“Cas, it’s fine. We can explain it to people when we’re ready.” Castiel liked that about Dean. Dean was making sure that he was being taken care of.   
They made it to their reservations on time, and were seated. The valet almost wasn’t allowed to take Dean’s car, but Castiel made him hand over his keys so they could get inside. Once inside and at their table, the two fell into easy conversation. Castiel filled Dean in on his day of work. Dean told Castiel about his meetings with some of his clients. He didn’t go into detail, but Castiel asked what he thought were the right questions. Dean smiled and answered them all. 

“So, can I ask you something?” Castiel took a sip of his whiskey, which he had acquired a taste for over the weekend. 

“Of course,” Dean replied. 

“The night that we were supposed to meet, and you cancelled on me, why did you cancel on me?” 

“Oh,” Dean took a drink and looked at Castiel across the table. “To be honest? I got a call from my brother. He’d gotten broken up with by his horrible girlfriend, Ruby. Nobody liked her, but Sam was always kind of the rebel, believe it or not. He needed me, so I’m really sorry that I did, but if we’re going to be together, you should know that he comes first.” Castiel nodded. For some reason, he felt this had been very difficult for Dean to confess. 

“That’s good to know. Thank you for sharing that.” The rest of the night was easy. The two had good conversation and they were done eating, Dean stood up and pulled the chair out for Castiel. The two walked back, hand-in-hand, to the valet stand. Dean finally got his car back, and they drove back to Castiel’s. Dean walked Castiel up to his door and the two smiled. 

“Well, Cas, I…I want to come inside, but I also want us to take this dating thing more seriously. And, if it’s okay with you, I’d like to take it slower, and just give you a kiss goodnight.” Dean leaned over and pressed a gentle kiss to Castiel’s lips. Castiel kissed him back, and just when he wanted to push it further, Dean pulled back with a smile.   
“Damn it, Cas. You might be the death of me someday.” 

“As long as that day is far, far away.” Castiel pressed his lips to Dean’s once more.

**Notes for the Chapter:**

> Again, sorry for the tardiness! I think this only has one more chapter, unfortunately (or fortunately, depending if you're actually enjoying). Anyway, THANK YOU all! You're the best and I love you ALL!


	17. Chapter 17

ONE MONTH LATER  
Dean sighed and looked in the mirror. This was it. This was his last date. Then he would be at the garage full time and he wouldn’t have to lie to people anymore. He wouldn’t have to lie about who he was dating or what he did for a living. He could finally be honest. He was dating an amazing man that he was falling for (maybe a month was too soon for the word love, but he was definitely falling into something), he would have a great job with his uncle and one of his best friends, what more could somebody ask for?   
He walked out to his car and got in. He was meeting this woman (Celeste) at a bar with her parents. Apparently, she was a lesbian, but didn’t want her parents to know, so in stepped Dean. “An easy one” Meg had said. His last date and an easy dinner with the folks that would not lead anywhere, for sure. He drove to the bar and looked around for “striking red hair” as she had described herself. He saw one girl that fit that, but she was sitting by herself at a high-topped table. She waved him over and Dean walked over. 

“Hi, are you Celeste?” The girl took a sip of something that looked fruity and sugary, then nodded and offered her hand. 

“I am, and call me Charlie.” Dean took and shook her hand before sitting down.

“Charlie,” Dean smiled. “Nice to meet you, Charlie. So, tell me about what the plan…” Charlie held up her hand. 

“The plan, sweetheart, is you’re going to tell me about what’s going on with you and my Cas.” Dean’s blood ran cold. HER Cas? 

“I…um…I didn’t know…Cas never told me that he was dating…” Charlie started laughing. 

“Oh, no no no no. Haha, no. Not my Cas in THAT way. I am actually a lesbian, didn’t they tell you that? I mean, he’s blowing me off for you, he and I have barely talked about anything BUT you, and what does that mean? I’m sure he’s talked about me, right?” Charlie raised an eyebrow at him and he chuckled. He remembered now. 

“Of course, he has. You’re his best friend. In fact, it was your idea that he come to Crowley’s in the first place, right?” Charlie beamed. 

“I did. My girlfriend had done an article on your place for her magazine…”

“Dorothy, right?” Charlie nodded before continuing.

“And I told him if he needed a date, why not give it a try. Little did I know that I’d be setting him up with the love of his life.” Dean blushed, just in time for the waitress to come over. 

“What can I get ya, hun?” 

“A whiskey, neat.” Dean looked over at Charlie’s glass and noticed it was almost empty. “And another one of whatever she was having.” The waitress looked at Charlie, waiting for he to respond. 

“Bahama Mama.” Charlie answered. The waitress nodded and walked away. 

“The love of his life, huh?” Charlie shrugged and drank the remainder of her glass. 

“My opinion. I’ve heard him talk about people he was in love with, and then I heard him talk about you.” Charlie looked directly into Dean’s eyes. “The smile when he mentions your name, or when I ask him how you are. He has nothing but good things to say about you. He just seems…different now.” 

“Good different?” Dean asked sheepishly. The waitress dropped off their drinks. 

“Great different. He isn’t tied down with the Hannah thing anymore, he’s been talking to Gabriel and his parents more, he just…he’s happier.” Dean couldn’t help but grin. “Now, I’ve heard about you from Castiel, but the real reason that I wanted this was to get to know you. Who you are and what your intentions are with my Castiel?” Dean took a drink of his whiskey. 

“Well, my name is Dean Winchester. I’m an Aquarius, I like long walks on the beach,” 

“Stop. I want to know you. Your favorite things, where you grew up, your family, everything.” Dean smiled and dove into his life. He let Charlie know about things that he’d only told a few people. She was easy to open up to, and she reciprocated. By the end of the night, Dean felt like he might have had a new friend.   
Three whiskies and two Bahama Mamas later they were bonding over The Lord of the Rings when Charlie looked over her shoulder and smiled wide. 

“And I think that’s my cue to leave.” Dean glanced over his shoulder and held up his glass to the person that had just walked in. They walked over and looked between the two of them. 

“Hello, Dean. Charlie?” Castiel cocked an eyebrow at her. She giggled. 

“I wanted to meet him! It’s been a month and all I’ve heard is you talk about this guy and I wanted to meet him.” Charlie stood up and threw her arms around Dean. She pulled away after Dean gave her a squeeze and looked to Castiel. “And I approve. Matter fact, if I was straight, you’d have some competition, but since I’m not, we should go on a double date! Soon!” Charlie clapped her hands and Castiel laughed. 

“Is Dorothy going to pick you up?” 

“No, I’m fine. I really need to get going though. She’ll kill me if I’m late. I’ll see you guys at our double date!” Charlie waved, gave Castiel a kiss on the cheek, and walked out. Castiel took Charlie’s now empty seat. 

“I thought this was your last day at work.” Dean grinned. 

“It was.” Dean nodded towards the door as he finished off his whiskey. “That was my last date, and I’m realizing now that I’ve got to pay for her drinks.” 

“Oh, she’ll love you for that.” The waitress came again. 

“Another drink for you, sweetheart?”

“Make it two,” Castiel replied. The waitress smiled at him and walked away. “So, you got the third degree from Charlie, huh?” Dean chuckled. 

“If you could call it that. She’s sweet. And worried about you. She just wanted to make sure that I’m good enough for you, I guess.” 

“And you got her to like you. That’s great.” Castiel smiled. He hadn’t dated since being in Chicago, but he knew that he wanted Charlie’s approval. The two continued their night, turning it into a date and if Castiel ended up in Dean’s bed for the night, so be it. 

 

TWO YEARS LATER  
Dean slammed the hood of the car he’d been working on for the past two hours. His back ached, his hands were covered in grease, and he was physically exhausted, but it was the happiest he had been at work. Working with Bobby and Benny made the days go by much faster and he actually enjoyed it. He loved his job, and he loved his boyfriend. Castiel and Dean had been living together for almost a year now, and Dean enjoyed every second of it. 

“So, ya ready for tonight?” Benny smacked Dean on the back. Dean smiled. 

“Yeah, gotta pick up the Novaks at the airport in an hour before Cas gets off. You’re still okay with them hiding out with you until the party?” 

“Yup! Sam’s gettin things set up with Ellen at The Roadhouse.”

“You two idjits gonna keep yappin’ or ya gonna get some work done?” Bobby called from the office. 

“We’re done, old man!” Dean yelled back. It was true. Dean had been finishing up the last car that was in the garage. 

“Then get your asses in here and help me with the inventory!” Benny and Dean rolled their eyes, but went into Bobby’s office. 

“Actually, Dean, you go get cleaned up. You look like hell.” 

“Gee, thanks, Bobby.” Dean knew that it was actually meant as a dismissal from work. It was Bobby’s way of telling him that he needed to go and get ready. “I’ll see you guys at The Roadhouse, right?” 

“Yeah, yeah, just go get ready, lover boy.” Benny whipped his rag at Dean and chased him out of the garage. 

An hour later, Dean was waiting by the luggage carousel, waiting for Chuck, Becky, and Gabriel to arrive. Gabriel was coming from California, but he had managed to get a flight that had a close arrival time to his parents. Dean had invited Michael and he had politely declined. Via email. Which Dean considered to better than what could have happened. Lucifer was still missing, according to the family, but to be honest, they were the only ones that Dean wanted there were going to be there. 

Dean saw Gabriel first. He was bouncing on the balls of his feet coming down the escalator. He came down and ran to Dean, wrapping his arms around him. 

“DEAN-O!” Dean laughed and hugged Gabriel back. 

“Hey, Gabriel, take it easy, man.” Gabriel pulled away, beaming. 

“I know, I know. I’m just so excited to be a best man, and I’ve got my speech all planned out already, and…” 

“I haven’t even asked him, yet. Calm down.” Gabriel rolled his eyes, but grinned. 

“He’ll say yes. Now where are my parents?” Dean looked over Gabriel’s head, but didn’t see Chuck and Becky yet. 

“Not here yet, still waiting.” 

“How did I beat them here? Anyway, let’s grab my bags.” 

“Bags?! You’re only here for a few days!”

“I know that,” Gabriel replied calmly, “but one never knows which occasions may arise.” Dean rolled his eyes, but followed Gabriel to the luggage carousal. They made small talk about Gabriel’s most recent play, his latest fling (his own understudy) , and what Dean and Castiel had been up to. 

“So, who’s all going to be here?” 

“Well, you, your parents, my Aunt Ellen, my Uncle Bobby, my brother Sam, my best friends Jo and Benny, Castiel’s best friend Charlie, her girlfriend Dorothy, um…”

“Did he already mention us?” A voice behind Dean asked. They turned and smiled at Becky and Chuck. They all hugged and then grabbed everybody’s bags. They were walking out to Dean’s car as Becky and Chuck filled them in about everything happening in Wisconsin. 

“…gave him a piece of my mind, I’ll tell you that! I’m just glad to be getting away for a few days. So, where will we be going?” Becky asked, once inside the car. 

“My friends’ place. Jo Harvelle and Benny Lafitte. They’ll drive you to The Roadhouse, and Cas and I will show up soon after.” 

“That sounds fun.” Chuck smiled. Dean drove to Jo and Benny’s apartment. They carried everything up to the apartment and knocked. Jo answered the door and smiled at them all. 

“Hello, soon-to-be in-laws!” Jo pushed Dean out of the way and hugged Gabriel first and then Chuck and Becky. 

“Really? That’s rude.” Dean commented before they all walked in the apartment. “Anyway, Gabriel, Chuck, Becky, this is one of my best friends, Jo Harvelle. Jo, this is Gabriel, Chuck, and Becky Novak. Cas’ family.” Dean had gestured to each of the Novaks in turn. 

“Seriously, it’s so nice to meet you all. And I’m glad this day is finally here. Dean’s been, well as my boyfriend would say, jitterier than a rabbit in a snake’s hole.” Dean blushed and gave Jo’s shoulder a shove. 

“I have not been.” However, that was a lie. Ever since Dean had asked Chuck and Becky (and Gabriel) for Cas’ hand (God, that still sounded so cheesy, even in Dean’s head), he’d been freaking out about it. He didn’t know how to do it, until Gabriel gave him some advice. 

“Castiel won’t care how you do it, as long as it’s you doing it.” With that in mind, Dean decided the best place to do it was a place they had been many times. A place that they both loved and had people that they loved there. The Roadhouse. 

Dean left when Gabriel and Jo were discussing the best drinks that they’ve ever had. He needed to get home before Castiel did, otherwise none of it would work. Castiel would be suspicious, and then not want to go out. Dean took a deep breath before walking into their house. How was he going to keep his cool for the hour before they were going to leave. Dean ran up to their room and grabbed the ring box out of his little hidey hole in the floor that he’d discovered after they had moved in. He opened it up and glanced in. Still inside, was a thin black tungsten ring. It was more Castiel’s style than anything the girl at the jewelry shop had shown him. He also received confirmation from Charlie and Gabriel that Castiel would love it. 

“Dean!” Castiel called. Dean placed the box in his pocket and came out to the living room.

“Hi, sunshine. How was work?” Dean walked over and gave Castiel a kiss. Castiel sighed. 

“Long. Difficult. You?” Dean shrugged. 

“Bobby yelled, Benny talked, I actually worked. The usual. But, they want to go out to The Roadhouse.” Castiel groaned. 

“I just want to relax with you on the couch. Why don’t you go and I’ll stay here and we can have fun when you get home?” Castiel attempted to waggle his eyebrows. Dean almost started sweating. 

“No, come on, Benny and Jo want to see you.” 

“Dean, I just…”

“Please, Cas? Just one beer, that’s all. I’ll even ride home with Benny so you can drive home whenever you want.” Castiel gave Dean a glare for a moment before walking up the stairs. “Where are you going?” Dean yelled after him. 

“To get ready for the stupid Roadhouse!” Dean smiled, happy he’d gotten Castiel to agree to go. He took a deep breath and sat down. He began rehearsing the speech again.   
“Cas, I love you, and you’ve made me a better person. I want…I want to spend the rest of my life with you. Get down on your knee and bam. Right. Okay.” Dean sighed. 

“Ready?” Dean called up to Castiel. Castiel came bounding down the stairs. He was rolling up the sleeves of his white button up. He held out his hands. 

“Ta-da. Let’s go. The sooner we get there the sooner we can leave.” Castiel grabbed Dean’s hand and pulled him out the door. 

“There are a lot of people here tonight.” Castiel commented when they pulled in to the parking lot. There were a few more cars there than normal, but the bar was actually closed down for the party tonight. Dean parked the car, and the two sat in silence for a moment. Suddenly, Dean felt Castiel’s hand on his knee. Dean looked at it, and then at Castiel. 

“Your knee was bouncing.” Castiel smiled and Dean couldn’t help but smile back. 

“Sorry, ready to go?” Castiel sighed and nodded. The two got out of the car and walked up to the saloon doors, and then through them. 

“SURPRISE!” Everybody yelled. Castiel jumped slightly, and Dean grabbed his hand and laughed. 

“Castiel!” Becky and Chuck broke away from everybody walked over to them. 

“Mom? Dad? What are you doing here?” 

“Oh well, your father just finished another book and I want to take a break before I try to get through it.” 

“Rude.” Chuck pouted for a moment and then hugged his son. Becky did the same, and then gave Dean a kiss on the cheek. 

“Good to see you two.” 

“Yeah, I…”

“CASSIE!” Dean was being pushed aside as Gabriel threw his arms around his brother. 

“You’re here, too?” Castiel raised an eyebrow, and Gabriel waggled his. 

“Oh yeah. Mom and Dad invited me to crash everything.” 

“Crash what, exactly?” Castiel shot a glance to Dean, but Dean just smiled. 

“I’ll grab us some drinks. Beer? Something stronger?”

“Beer is fine, thank you.” Castiel was still looking around suspiciously. 

“So, answer this question for your big bro.” Castiel met Gabriel’s eyes and Gabriel nodded over Castiel’s shoulder where Dean was talking to a man that was taller than him with shaggy brown hair. “Who’s your boy toy talking to?” Castiel turned to look and then back to his brother. 

“That’s his younger brother Sam, and no.” 

“What do you mean?” Gabriel bat his eyes in an innocent way. 

“You want to hook up with Sam. And no. Leave him alone.” Gabriel rolled his eyes and held up his hands. 

“Fine.” 

“Everything alright?” Dean offered Castiel his beer. Castiel accepted it. 

“Gabriel wants to hook up with Sam.” Castiel took a sip of his beer while Dean shot daggers at Gabriel. Gabriel blushed and then held his hands up in defense. 

“All I asked was who he was. And now, I’m going to introduce myself.” Dean grabbed Gabriel’s arm and looked into his eyes. 

“No. I’ll go with you.” Dean kissed Castiel’s cheek and then Dean and Gabriel walked over to Sam. Sam smiled at both of them. 

“Hey, Dean.” 

“Sammy, this is Cas’ brother Gabriel, Gabriel, this is my little brother, Sammy.” Sam deadpanned at his older brother. 

“It’s Sam.” Sam offered his hand to Gabriel. Gabriel took and shook it.

“Nice to meet you. Pity we’re going to be brother-in-laws shortly.” Gabriel raked his eyes up and down Sam. Dean noticed Sam’s cheek tinge pink before he took a sip of his drink. 

“Are you done? I need to do this soon or I’m going to…I…I don’t know, but I’ll screw it up somehow.”

“Dean,” Sam put his hand on Dean’s shoulder and smiled. “Everything is going to be fine. He will say yes, and you will live happily ever after.” 

“That sounds like a chick-flick.” 

“You love chick-flicks.” Sam teased. Dean looked over at Castiel talking to his parents and Charlie. He watched Castiel snicker at something that Charlie had said as Dorothy joined them. 

“Alright, I’m going to do it now.” Dean walked over to the karaoke area and picked up the microphone. He flipped it on and there was a screech of feedback, getting everybody’s attention. 

“Hey, guys, I uh…I’m Dean, but you all knew that. I uh…I have called everybody here for, well, you all know why, except one of you. So, Cas?” Castiel’s eyes opened widely. “If you could come up here?” Castiel glanced at everybody, and Dean saw a look of realization come across his face. Castiel slowly walked up on the small platform and Dean couldn’t help but smile. 

“Cas,” Dean could feel his voice shaking. “I love you, and I’ve wanted to ask you this for a while now, so, Angel,” Dean pulled the box out of his pocket and fell to one knee. Castiel’s eyes watered and Dean’s vision began to swim as well. “Will you marry me?” 

“Of course, I’ll marry you.” Castiel whispered with a nod. He didn’t trust his voice. He held out his hand and Dean slipped the ring on, and the entire bar broke out into applause. Dean stood up and kissed his fiancé. The first people to hug them when they got off the stage was Becky and Chuck. Becky hugged Castiel first and then hugged Dean.

“I’m so happy he found you.” She whispered in Dean’s ear. Dean pulled away and looked at her. She had a genuine smile on her face and tears in her eyes. “Welcome to our family, Dean.” Dean hugged her again. 

The rest of their friends and family gave them hugs and handshakes and congratulations, but none of them had touched Dean the way that Becky’s words had. She had finally come around to Castiel being happy without Hannah. 

“Drinks on the house all night!” Ellen called and everybody cheered again. 

Some people left and came back, but around midnight, it was just the family. 

“So, Cassie, I’m assuming your wedding is going to be big and expensive?” Gabriel asked at the bar. Castiel rolled his eyes. 

“Yes, because Dean and I are like that.” Gabriel shrugged. 

“You never know. Maybe Dean is a diva and wants to have a big swanky wedding. You might have to get a second job.” 

“I could just have Dean be a hooker again.” Castiel replied with a sip of his beer. 

“…What do you mean, again?” Castiel sighed and looked at his family. They were all staring at him, but Dean’s family had amused grins on their faces. 

“We preferred the term escorts, Cas.” Dean smiled. 

“I…this…I am so confused.” 

“Well then, gather ‘round, and I’ll tell you the real story of how Cas and I met.”

**Notes for the Chapter:**

> FINALLY! I am so so sorry, you guys (I know some of you have told me not to worry about it, but I still feel bad). I have been dealing with family madness, and work craziness, and other things that you guys don't need to worry about. Anyway! The last chapter is finally here and I hope you guys enjoy it. Thank you ALL for reading, commenting, leaving kudos, and loving this story. It means the world to me. I love you guys, and can't thank you enough.

**Author's Note:**

> Hi, guys. So this is my first story that I'm posting on here. I'm planning on uploading every Monday, but life gets crazy. Please let me know what you think. I would greatly appreciate it! Thanks for reading!


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